2-Phenylisobutyric acid → HCID 66590192, compound

HRID 2363462Notes

Reaction equation

HRID 2363462 reaction equation
[CH2:1]([N:8]1[CH2:12][C@H:11]2[C@H:13]([NH2:16])[CH2:14][CH2:15][C@H:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][C:18]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH3:22])[C:19](O)=[O:20].C1([C@H](CC)C(O)=O)C=CC=CC=1>>[CH2:1]([N:8]1[CH2:12][C@@H:11]2[C@@H:13]([NH:16][C:19](=[O:20])[C:18]([CH3:17])([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH3:22])[CH2:14][CH2:15][C@@H:10]2[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 132222-Phenylisobutyric acidHCID 785329(S)-2-Phenylbutyric acidHCID 25918977(3aS,4R,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine

Product 1

HCID 66590192HCID 66590192, compound

Procedure

The title compound was prepared by substituting (3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine from Step A of Example 33 for (3aS,4R,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine and 2-methyl-2-phenylpropanoic acid for (S)-2-phenylbutanoic acid in Step F of the procedure used to prepare Example 16: 1H NMR (400 MHz, pyridine-d5) δ ppm 7.49-7.38 (m, 4H), 7.31 (ddd, J=7.3, 14.4, 22.5, 5H), 7.08 (d, J=7.3, 1H), 4.46-4.35 (m, 1H), 3.58 (d, J=13.2, 1H), 3.43 (d, J=13.2, 1H), 2.84 (d, J=6.7, 1H), 2.36 (d, J=4.8, 3H), 2.31 (d, J=9.6, 1H), 2.21-2.13 (m, 1H), 2.04 (td, J=5.9, 11.7, 1H), 1.70 (dd, J=6.7, 12.3, 1H), 1.67 (s, 6H), 1.53-1.41 (m, 1H), 1.38-1.26 (m, 1H); MS (ESI+) m/z 363 (M+H)+.

Workup

  1. customto prepare Example 16

Sources & evidence

ORD record
ord-310bdad6f28e48f2808da3797848669b
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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