Reaction #3165466
Related Literature (1)
openreactiondata ↗doi:10.6084/m9.figshare.5104873.v1; patent:US09193762B2
Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: From benzylamine. (87%); 1H NMR (400 MHz, CDCl3) δ 7.55 (bd, J=6.3 Hz, 1H), 7.31 (m, 4H), 7.28-7.14 (m, 6H), 5.21-5.07 (m, 1H), 5.07-4.88 (m, 1H), 4.71-4.48 (m, 1H), 4.48-4.14 (m, 3H), 3.71 (dd, J=16.5, 8.6 Hz, 1H), 3.66-3.43 (m, 3H), 3.43-3.22 (m, 1H), 2.62-1.96 (m, 4H), 1.96-1.33 (m, 4H). MS (ESI+) m/z 458.1; calcd for C25H29N3O4Na (MNa+): 458.21. RS-33-2: (S)-benzyl 2-((S)-2-((3,4-dichlorobenzyl)carbamoyl)pyrrolidine-1-carbonyl) pyrrolidine-1-carboxylate. From 3,4-dichlorobenzylamine. (69%); 1H NMR (400 MHz, CDCl3) δ 7.87 (t, J=5.9 Hz, 1H), 7.53-7.18 (m, 7H), 7.18-6.82 (m, 1H), 5.20-5.06 (m, 1H), 5.06-4.91 (m, 1H), 4.67-4.48 (m, 1H), 4.48-4.28 (m, 2H), 4.28-4.13 (m, 1H), 3.78-3.23 (m, 4H), 2.58-2.05 (m, 3H), 2.05-1.41 (m, 5H). MS (ESI+) m/z 526.08, 528.08; calcd for C25H27Cl2N3O4Na (MNa+): 526.13, 528.13. RS-33-3: (S)-benzyl 2-((S)-2-((4-chlorophenethyl)carbamoyl)pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylate. From 4-chlorophenethylamine. (75%); 1H NMR (500 MHz, CDCl3) δ 7.86 (bs, 1H), 7.39-7.03 (m, 9H), 5.25-4.91 (m, 2H), 4.63-4.27 (m, 1H), 4.27-3.90 (m, 1H), 3.77-3.19 (m, 6H), 2.94-2.66 (m, 2H), 2.56-1.94 (m, 4H), 1.94-1.21 (m, 4H). MS (ESI+) m/z 506.0; calcd for C26H30ClN3O4Na (MNa+): 506.18. RS-33-4: (S)-benzyl 2-((S)-2-((2-methoxyphenethyl)carbamoyl)pyrrolidine-1-carbonyl) pyrrolidine-1-carboxylate. From 2-methoxyphenethylamine. (84%); 1H NMR (500 MHz, CDCl3) δ 7.36-7.29 (m, 5H), 7.20-7.09 (m, 2H), 6.94 (bs, 1H), 6.88-6.80 (m, 2H), 5.41-4.85 (m, 2H), 4.67-3.93 (m, 2H), 3.81 (s, 3H), 3.74-3.22 (m, 6H), 3.11-2.70 (m, 2H), 2.53-1.22 (m, 8H). MS (ESI+) m/z 502.1; calcd for C27H33N3O5Na (MNa+): 502.23. RS-33-5: (S)-benzyl 2-((S)-2-(decylcarbamoyl)pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylate. From n-decylamine. (66%); 1H NMR (400 MHz, CDCl3) δ 7.70 (s, 1H), 7.29 (m, 5H), 5.29-4.89 (m, 2H), 4.68-4.15 (m, 2H), 3.82-3.03 (m, 6H), 2.61-1.63 (m, 8H), 1.60-1.14 (m, 16H), 0.87 (dd, J=7.9, 4.5 Hz, 3H). MS (ESI+) m/z 508.2; calcd for C28H43N3O4Na (MNa+): 508.31. RS-33-6: (S)-benzyl 2-((S)-2-(hexadecylcarbamoyl)pyrrolidine-1-carbonyl) pyrrolidine-1-carboxylate. From hexadecylamine (68%) 1H NMR (400 MHz, CDCl3) δ 7.40 (bs, 5H), 7.08 (bs, 1H), 5.27-4.84 (m, 2H), 4.73-4.07 (m, 2H), 3.81-3.00 (m, 6H), 2.57-1.60 (m, 8H), 1.25 (bs, 28H), 0.85 (t, J=5.8 Hz, 3H). MS (ESI+) m/z 592.69; calcd for C34H55N3O4Na (MNa+): 592.41. RS-33-7: (S)-benzyl-2-((S)-2-(pentadecylcarbamoyl)pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylate. From pentadecylamine (66%) 1H NMR (400 MHz, CDCl3) δ 7.36-7.30 (bs, 5H), 7.10 (bs, 1H), 5.25-4.91 (m, 2H), 4.65-4.13 (m, 2H), 3.78-3.03 (m, 6H), 2.58-1.81 (m, 8H), 1.25 (bs, 26H), 0.88 (t, J=6.7 Hz, 3H). MS (ESI+) m/z 578.3; calcd for C33H53N3O4Na (MNa+): 578.39. RS-33-8: (S)-benzyl 2-((S)-2-((2-methoxy-5-(trifluoromethyl)phenyl)carbamoyl)pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylate. From 2-methoxy-5-(trifluoromethyl)aniline. (35%); 1H NMR (400 MHz, CDCl3) δ 9.22 (bd, 1H), 8.66 (dd, J=12.8, 1.4 Hz, 1H), 7.87-7.03 (m, 6H), 6.87 (dd, J=8.5, 3.1 Hz, 1H), 5.09 (m, 3H), 4.90-4.37 (m, 2H), 4.02-3.80 (m, 3H), 3.76-3.22 (m, 3H), 2.53-0.77 (m, 8H).
Source ID: ord-14440aa935774b4893a3edb26e176c02