(R)-2-methyl-1-((S)-pyrrolidin-2-ylmethyl)pyrrolidine → [4-(6-Methoxy-pyridin-2-yl)-phenyl]-[2-(S)-(2-(R)-Methyl-pyrrolidin-1-ylmethyl)-pyrrolidin-1-yl]-methanone

HRID 1867860Notes

Reaction equation

HRID 1867860 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=1.[CH3:18][C@@H:19]1[CH2:23][CH2:22][CH2:21][N:20]1[CH2:24][C@@H:25]1[CH2:29][CH2:28][CH2:27][NH:26]1>>[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]2[CH:10]=[CH:11][C:12]([C:13]([N:26]3[CH2:27][CH2:28][CH2:29][C@H:25]3[CH2:24][N:20]3[CH2:21][CH2:22][CH2:23][C@H:19]3[CH3:18])=[O:15])=[CH:16][CH:17]=2)[CH:6]=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 46911921(R)-2-methyl-1-((S)-pyrrolidin-2-ylmethyl)pyrrolidineHCID 534263354-(6-Methoxypyridin-2-yl)benzoic acid

Product 1

HCID 57980055[4-(6-Methoxy-pyridin-2-yl)-phenyl]-[2-(S)-(2-(R)-Methyl-pyrrolidin-1-ylmethyl)-pyrrolidin-1-yl]-methanoneYield 76%

Procedure

The title compound is prepared in a manner substantially analogous to General Procedure B′ using 4-(6-Methoxy-pyridin-2-yl)-benzoic acid (573 mg, 2.5 mmol) and 2-(R)-methyl-1-(2-(S)-pyrrolidinylmethyl)pyrrolidine (337 mg, 2.0 mmol) to give 580 mg (76% yield). MS (ES+) 380.2 (M+H)+

Workup

  1. customto give 580 mg (76% yield)

Sources & evidence

ORD record
ord-e0528f5b9b464a049329f5699dae7a2f
Source dataset
uspto-grants-2009_12
Patent number
US07632857B2

Reaction notes

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