1-Phenylcyclopentanecarboxylic acid → N-[(3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-yl]-N,3-dimethyl-2-phenylbutanamide

HRID 2363535Notes

Reaction equation

HRID 2363535 reaction equation
[C:1]1([C:7]2([C:12]([OH:14])=O)[CH2:11][CH2:10]CC2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:15]([N:22]1[CH2:26][C@@H:25]2[C@@H:27]([NH:30][CH3:31])[CH2:28][CH2:29][C@@H:24]2[CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH2:32](N1C[C@H]2C(N)CC[C@H]2C1)C1C=CC=CC=1>>[CH2:15]([N:22]1[CH2:26][C@@H:25]2[C@@H:27]([N:30]([CH3:31])[C:12](=[O:14])[CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:11]([CH3:10])[CH3:32])[CH2:28][CH2:29][C@@H:24]2[CH2:23]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 3

HCID 661671-Phenylcyclopentanecarboxylic acidHCID 66591269(3aR,4S,6aS)-2-benzyl-N-methyloctahydrocyclopenta[c]pyrrol-4-amineHCID 68411161(3aS*,6aR*)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine

Product 1

HCID 66590058N-[(3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-yl]-N,3-dimethyl-2-phenylbutanamide

Procedure

The title compound was prepared by substituting 3-methyl-2-phenylbutanoic acid for 1-phenylcyclopentanecarboxylic acid and (3aR,4S,6aS)-2-benzyl-N-methyloctahydrocyclopenta[c]pyrrol-4-amine from Step B for (3aS*,6aR*)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine in the procedure described in Example 2: 1H NMR (300 MHz, CDCl3) δ ppm 7.59-7.41 (m, 5H), 7.39-7.16 (m, 5H), 3.64 (d, J=13.2, 1H), 3.50 (d, J=9.5, 1H), 2.69-2.52 (m, 2H), 2.50-2.33 (m, 3H), 2.25-2.15 (m, 1H), 2.05 (dd, J=6.3, 9.2, 1H), 1.88-1.67 (m, 2H), 1.34 (dd, J=13.4, 19.6, 3H), 1.08 (d, J=6.4, 3H), 1.03-0.95 (m, 1H), 0.79-0.66 (m, 6H); MS (ESI+) m/z 391 (M+H)+.

Sources & evidence

ORD record
ord-9dd0aab19de649a5851062993a9d59c8
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

Loading…