N,N-Diethyl-2,3-dimethylbenzamide → (R)-3-[3-(2-hydroxymethylpyrrolidin-1-yl)propyl]-2H-isoquinolin-1-one

HRID 2373261Notes

Reaction equation

HRID 2373261 reaction equation
C([N:3]([CH2:14][CH3:15])[C:4](=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7](C)[C:6]=1[CH3:12])C.[OH:16][CH2:17][C@H:18]1[CH2:22][CH2:21][CH2:20][N:19]1[CH2:23][CH2:24]CC#N>>[OH:16][CH2:17][C@H:18]1[CH2:22][CH2:21][CH2:20][N:19]1[CH2:23][CH2:24][CH2:15][C:14]1[NH:3][C:4](=[O:13])[C:5]2[C:6]([CH:12]=1)=[CH:7][CH:8]=[CH:9][CH:10]=2

Participants

3

Reactant 2

HCID 15621069N,N-Diethyl-2,3-dimethylbenzamideHCID 62733483(R)-4-(2-hydroxymethylpyrrolidin-1-yl)butyronitrile

Product 1

HCID 10379255(R)-3-[3-(2-hydroxymethylpyrrolidin-1-yl)propyl]-2H-isoquinolin-1-oneYield 16.8%

Procedure

By the reaction in the same manner as in Example 1a, using N,N-diethyl-2,3-dimethylbenzamide (5.0136 g) and (R)-4-(2-hydroxymethylpyrrolidin-1-yl)butyronitrile (2.2 g), (R)-3-[3-(2-hydroxymethylpyrrolidin-1-yl)propyl]-2H-isoquinolin-1-one (627.3 mg) was obtained. 1N aqueous HCl solution (2.4 ml) was added thereto in an acetone solvent, and the precipitated crystals were collected by filtration to give (R)-3-[3-(2-hydroxymethylpyrrolidin-1-yl)propyl]-2-isoquinolin-1-one hydrochloride (555.3 mg).

Workup

  1. customBy the reaction in the same manner as in Example 1a

Sources & evidence

ORD record
ord-72feeff25e9241489d64592494b8aaee
Source dataset
uspto-grants-2008_12
Patent number
US07459465B2

Reaction notes

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