Benzaldehyde, 4-(phenylmethoxy)- → 1-(4-(Benzyloxy)benzyl)-5-(2,6-dimethoxyphenyl)pyrrolidin-2-one

HRID 594665Notes

Reaction equation

HRID 594665 reaction equation
[NH2:1][CH:2]([C:9]1[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=1[O:17][CH3:18])[CH2:3][CH2:4][C:5]([O:7]C)=O.[CH2:19]([O:26][C:27]1[CH:34]=[CH:33][C:30]([CH:31]=O)=[CH:29][CH:28]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[CH2:19]([O:26][C:27]1[CH:28]=[CH:29][C:30]([CH2:31][N:1]2[CH:2]([C:9]3[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=3[O:17][CH3:18])[CH2:3][CH2:4][C:5]2=[O:7])=[CH:33][CH:34]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

3

Reactant 2

HCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 69082397Methyl 4-amino-4-(2,6-dimethoxyphenyl)butanoate

Product 1

HCID 690857521-(4-(Benzyloxy)benzyl)-5-(2,6-dimethoxyphenyl)pyrrolidin-2-oneYield 55%

Procedure

1-(4-(benzyloxy)benzyl)-5-(2,6-dimethoxyphenyl)pyrrolidin-2-one was prepared according to the described general procedure 2 (GP2) by reaction of methyl 4-amino-4-(2,6-dimethoxyphenyl)butanoate (400 mg; 1.38 mmol) with commercially available 4-(benzyloxy)benzaldehyde (293 mg; 1.38 mmol). Subsequent purification by preparative HPLC afforded 1-(4-(benzyloxy)benzyl)-5-(2,6-dimethoxyphenyl)pyrrolidin-2-one (316 mg; 55%). LC-MS (conditions A): tR=0.91 min.; [M+H]+: 417.76 g/mol.

Workup

  1. custom1-(4-(benzyloxy)benzyl)-5-(2,6-dimethoxyphenyl)pyrrolidin-2-one was prepared
  2. customSubsequent purification by preparative HPLC

Sources & evidence

ORD record
ord-40f6be9018cf41f294b189fc2d6957d3
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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