Electronic Supplementary Information. Carbon dioxide as a reversible amine-protecting
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1 Electronic Supplementary Information Carbon dioxide as a reversible amine-protecting agent in selective Michael additions and acylations Annelies Peeters, Rob Ameloot and Dirk E. De Vos * Centre for Surface Chemistry and Catalysis, KU Leuven, Kasteelpark Arenberg 23, 3001 Leuven, Belgium 1
2 NMR study of compounds under air and under CO 2 atmosphere 1 H-NMR spectra of products were recorded on a Bruker AMX-300 at 300 MHz and 13 C-NMR spectra at 75.5 MHz. Samples were prepared by dissolution of 20 µl of the sample in 600 µl of d-dmso or d- acetonitrile. To study the reaction of the product with CO 2, samples were bubbled at room temperature with CO 2 for approximately 2 minutes. After bubbling, the solution was transferred to an NMR tube and sealed immediately and spectra were recorded as soon as possible. Figure SI.1 1 H NMR spectra of cyclohexylamine in d-dmso (top) and after flushing with CO 2 at room temperature and atmospheric pressure (bottom) Figure SI.2 13 C-NMR spectra of cyclohexylamine in d-dmso (top) and after flushing with CO 2 at room temperature and atmospheric pressure (bottom) 2
3 Figure SI.3 1 H NMR spectra of octylamine in d-dmso (top) and after flushing with CO 2 at room temperature and atmospheric pressure (bottom) Figure SI.4 13 C-NMR spectra of octylamine in d-dmso (top) and after flushing with CO 2 at room temperature and atmospheric pressure (bottom) Figure SI.5 1 H NMR spectra of morpholine in d-dmso (top) and after flushing with CO 2 at room temperature and atmospheric pressure (bottom) 3
4 Figure SI.6 1 H NMR spectra of p-isopropylaniline in d-dmso (top) and after flushing with CO 2 at room temperature and atmospheric pressure (bottom) Figure SI.7 1 H NMR spectra of p-toluenesulfonamide in d-acetonitrile (top) and after flushing with CO 2 at room temperature and atmospheric pressure (bottom) Figure SI.8 1 H NMR spectra of ethylacetoacetate in d-acetonitrile (top) and after flushing with CO 2 at room temperature and atmospheric pressure (bottom) 4
5 Identification of products methyl 3-(N-benzylamino)propionate GC-MS (EI, 70eV): m/z (rel. int.): 193 (1 %) [M + ], 192 (2), 120 (16), 106 (28), 102 (5), 91 (100), 77 (6), 65 (18). 3,3'-(N-benzylimino)dipropionic acid dimethyl ester GC-MS (EI, 70eV): m/z (rel. int.): 279 (2 %) [M + ], 206 (55), 192 (11), 91 (100), 65 (6). methyl 3-(N-cyclohexylamino)propionate GC-MS (EI, 70eV): m/z (rel. int.): 185 (11 %) [M + ], 156 (6), 142 (100), 129 (4), 112 (26), 110 (21), 82 (16), 68 (42), 56 (47), 41 (62). methyl 3-(N-hexylamino)propionate GC-MS (EI, 70eV): m/z (rel. int.): 187 (2 %) [M + ], 172 (2), 158 (2), 144 (1), 130 (2), 116 (100), 114 (21), 102 (5), 84 (77), 70 (9), 56 (33), 42 (99). 3,3'-(N-hexylimino)dipropionic acid dimethyl ester GC-MS (EI, 70eV): m/z (rel. int.): 273 (1 %) [M + ], 202 (100), 200 (57), 160 (9), 130 (50), 116 (11), 98 (7), 84 (22), 70 (6), 59 (30), 55 (40), 42 (69). methyl 3-(N-octylamino)propionate GC-MS (EI, 70eV): m/z (rel. int.): 215 (2 %) [M + ], 172 (2), 158 (2), 142 (15), 128 (3), 116 (100), 84 (55), 70 (10), 56 (21), 42 (71). 3,3'-(N-octylimino)dipropionic acid dimethyl ester GC-MS (EI, 70eV): m/z (rel. int.): 301 (1 %) [M + ], 258 (1), 228 (36), 202 (100), 160 (8), 130 (35), 116 (9), 84 (16), 55 (22), 42 (39). 5
6 methyl 3-(dipropylamino)propionate GC-MS (EI, 70eV): m/z (rel. int.): 187 (4 %) [M + ], 172 (2), 158 (100), 144 (1), 130 (7), 114 (48), 84 (26), 70 (7), 59 (5), 42 (42). methyl 3-(piperidino)propionate GC-MS (EI, 70eV): m/z (rel. int.): 171 (6 %) [M + ], 156 (2), 98 (100), 96 (8), 84 (3), 70 (3), 59 (4), 55 (12), 44 (9), 42 (18). methyl 3-(morpholinyl)propionate GC-MS (EI, 70eV): m/z (rel. int.): 173 (4 %) [M + ], 142 (2), 115 (2), 100 (100), 88 (4), 84 (6), 70 (10), 56 (55), 42 (61). methyl 3-(p-toluenesulfonylamino)propionate GC-MS (EI, 70eV): m/z (rel. int.): 257 (1 %) [M + ], 226 (2), 184 (18), 155 (58), 102 (100), 91 (94), 77 (3), 70 (19), 65 (22). 3,3'-[p-toluenesulfonylimino]dipropionic acid dimethyl ester GC-MS (EI, 70eV): m/z (rel. int.): 343 (1 %) [M + ], 312 (2), 270 (29), 188 (87), 155 (65), 114 (35), 91 (100), 84 (20), 65 (16). 6
7 4-(aminomethyl)-1-piperidine propanoic acid methyl ester GC-MS (EI, 70eV): m/z (rel. int.): 200 (11 %) [M + ], 182 (5), 170 (5), 168 (5), 155 (3), 142 (11), 127 (89), 116 (22), 110 (100), 96 (51), 84 (20), 82 (15), 68 (8), 59 (7), 55 (23), 42 (32), 30 (24). NMR analysis of CO 2 -protected product. 1 H NMR (300 MHz, DMSO-d 6 ): δ 6.74 (NH-CO), 3.59 (s, O-CH 3 ), 2.8 (m, -CH 2 -NH-CO and N-CH 2 - in ring), 2.49 (m, N-CH 2 - in ring and N-CH 2 -CH2-CO-), 1.86 (t, J = 10.7 Hz, CH 2 -CO), 1.58 (d, J = 12.1, - CH 2 - in ring), 1.33 (m, -CH- in ring), 1.06 (m, -CH 2 - in ring). 4-[[(3-methoxy-3-oxopropyl)amino]methyl]-1-piperidine propanoic acid methyl ester GC-MS (EI, 70eV): m/z (rel. int.): 286 (7 %) [M + ], 255 (7), 227 (2), 213 (43), 133 (21), 182 (53), 171 (20), 155 (16), 142 (45), 116 (60), 112 (47), 110 (100), 98 (44), 96 (49), 84 (46), 82 (18), 70 (24), 55 (26), 42 (55), 30 (6) (((1-(3-methoxy-3-oxopropyl)piperidine-4-ylmethyl)azanediyl) dipropionic acid dimethyl ester GC-MS (EI, 70eV): m/z (rel. int.): 372 (2 %) [M + ], 341 (1), 313 (1), 299 (7), 285 (7), 202 (100), 182 (26), 170 (4), 155 (5), 142 (8), 110 (16), 96 (10), 55 (9), 42 (12), 30 (2). 7
8 methyl 3-(4-(2-aminoethyl)piperazine-1-yl)propanoate GC-MS (EI, 70eV): m/z (rel. int.): 215 (1 %) [M + ], 198 (8), 185 (94), 170 (15), 155 (8), 153 (8), 142 (46), 130 (9), 125 (4), 111 (50), 98 (100), 87 (11), 70 (35), 56 (37), 42 (47), 30 (21). methyl 3- (4-(2-((3-methoxy-3-oxopropyl)aminoethyl)piperazine-1-yl)propanoate GC-MS (EI, 70eV): m/z (rel. int.): 302 (1 %) [M + +1], 270 (7), 228 (16), 198 (8), 185 (100), 173 (11), 159 (8), 153 (8), 142 (10), 130 (8), 111 (31), 98 (59), 84 (13), 70 (19), 56 (24), 42 (31), 30 (3). dimethyl 3,3 -((2-4-(3-methoxy-3-oxopropyl)piperazin-1-yl)ethyl)azanediyl) dipropanoate GC-MS (EI, 70eV): m/z (rel. int.): 387 (1 %) [M + ], 314 (11), 245 (2), 228 (3), 216 (4), 202 (60), 185 (100), 170 (7), 153 (4), 142 (8), 130 (6), 111 (19), 98 (33), 84 (7), 70 (13), 55 (23), 42 (22), 30 (2). 8
9 methyl 3-((piperidine-2-ylmethyl)amino)propanoate GC-MS (EI, 70eV): m/z (rel. int.): 200 (1 %) [M + ], 169 (2), 127 (4), 118 (3), 96 (2), 84 (100), 56 (13), 42 (9), 30 (5). methyl 3-(2-(aminomethyl)piperidine-1-yl)propanoate GC-MS (EI, 70eV): m/z (rel. int.): 200 (1 %) [M + ], 170 (100), 142 (3), 127 (11), 110 (5), 96 (69), 84 (7), 68 (4), 55 (13), 42 (8), 30 (8). dimethyl 3,3 -((piperidine-2-ylmethyl)azanediyl)dipropanoate GC-MS (EI, 70eV): m/z (rel. int.): 286 (1 %) [M + ], 255 (2), 213 (6), 202 (11), 170 (1), 130 (33), 116 (2), 98 (2), 84 (100), 56 (11), 42 (9), 30 (4). methyl 3-(2-(((3-methoxy-3-oxopropyl)amino)methyl)piperidine-1-yl) propanoate GC-MS (EI, 70eV): m/z (rel. int.): 286 (1 %) [M + ], 255 (2), 213 (5), 170 (100), 142 (2), 110 (3), 96 (35), 84 (10), 68 (2), 55 (8), 42 (8), 30 (2). dimethyl 3,3 -(((1-(3-methoxy-3-oxopropyl)piperidine-2-yl)methyl)azanediyl) dipropanoate GC-MS (EI, 70eV): m/z (rel. int.): 372 (1 %) [M + ], 341 (1), 299 (4), 213 (1), 202 (4), 170 (100), 130 (2), 110 (2), 96 (20), 84 (4), 55 (8), 42 (7). 9
10 2-acetyl-pentanedioic acid 1-ethyl 5-methyl ester GC-MS (EI, 70eV): m/z (rel. int.): 216 (1 %) [M + ], 185 (2), 174 (6), 139 (11), 128 (7), 114 (6), 100 (21), 85 (6), 73 (5), 59 (13), 55 (20), 43 (100). 3-acetyl-1,3,5-pentanetricarboxylic acid 3-ethyl, 1,5 dimethyl ester GC-MS (EI, 70eV): m/z (rel. int.): 302 (1 %) [M + ], 271 (2), 214 (7), 200 (5), 186 (16), 171 (7), 155 (7), 143 (7), 127 (7), 113 (17), 97 (7), 81 (7), 67 (7), 59 (16), 55 (16), 43 (100). methyl 4-acetyl-5-oxohexanoate GC-MS (EI, 70eV): m/z (rel. int.): 186 (1 %) [M + ], 144 (13), 139 (1), 113 (11), 112 (12), 84 (15), 74 (3), 71 (11), 59 (9), 55 (18), 43 (10). 4,4-(diacetyl)heptanedioic acid dimethyl ester GC-MS (EI, 70eV): m/z (rel. int.): 272 (1 %) [M + ], 230 (3), 199 (5), 198 (5), 167 (3), 155 (2), 138 (7), 125 (13), 110 (4), 97 (13), 81 (2), 59 (7), 55 (7), 43 (100). acetic acid, phenylmethyl ester GC-MS (EI, 70eV): m/z (rel. int.): 150 (29%) [M + ], 108 (100), 91 (73), 90 (40), 79 (29), 77 (23), 65 (16), 63 (7), 51 (16), 43 (46). N-(phenylmethyl)-acetamide GC-MS (EI, 70eV): m/z (rel. int.): 149 (70%) [M + ], 106 (100), 91 (29), 79 (14), 77 (14), 65 (8), 51 (9), 43 (26). 10
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