HCID 67256139, compound → (3S)-1-(Phenylmethyl)-3-pyrrolidinyl 4-amino-3-methoxybenzoate

HRID 1821747Notes

Reaction equation

HRID 1821747 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][C:14](=[O:26])[C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[C:17]([O:24][CH3:25])[CH:16]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>B#[Ni]>[CH2:1]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][C:14](=[O:26])[C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[C:17]([O:24][CH3:25])[CH:16]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 67256139HCID 67256139, compound

Product 1

HCID 67254306(3S)-1-(Phenylmethyl)-3-pyrrolidinyl 4-amino-3-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 82791nickel boride (NiB)Catalyst

Procedure

The aniline was prepared by nickel boride reduction of 3-methoxy-4-nitro-benzoic acid (3S)-1-benzyl-pyrrolidin-3-yl ester analogously to the preparation of 4-[(Benzyl-methyl-amino)-methyl]-2-methoxy-phenylamine used in the synthesis of Compound 340. 1H-NMR (400 MHz, CDCl3) δ 7.54 (d, J=8.21 Hz, 1H), 7.44 (s, 1H), 7.2-7.4 (m, 5H) 6.65 (d, J=8.21 Hz, 1H), 5.38 (br.m, 1H), 4.22 (s, 1H), 3.90 (s, 3H), 3.69 (q, J=24.63 Hz, 1H), 3.0 (m, 1H), 2.7-2.9 (m, 2H), 2.5-2.6 (m, 1H), 2.3-2.4 (m, 1H), 1.9-2.1 (m, 1H). MS apci-pos (M+1=327.2.

Sources & evidence

ORD record
ord-e88e9acabe44443a906bf70a50668789
Source dataset
uspto-grants-2009_10
Patent number
US07608618B2

Reaction notes

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