N,N-Diethyl-2,3-dimethylbenzamide → (R)-3-(2-(2-(hydroxymethyl)pyrrolidin-1-yl)ethyl)-5-methylisoquinolin-1(2H)-one

HRID 2373279Notes

Reaction equation

HRID 2373279 reaction equation
C([N:3]([CH2:14][CH3:15])[C:4](=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[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]CC#N>>[OH:16][CH2:17][C@H:18]1[CH2:22][CH2:21][CH2:20][N:19]1[CH2:23][CH2:15][C:14]1[NH:3][C:4](=[O:13])[C:5]2[C:6]([CH:12]=1)=[C:7]([CH3:11])[CH:8]=[CH:9][CH:10]=2

Participants

3

Reactant 2

HCID 15621069N,N-Diethyl-2,3-dimethylbenzamideHCID 45088390(R)-3-(2-(Hydroxymethyl)pyrrolidin-1-yl)propanenitrile

Product 1

HCID 10424118(R)-3-(2-(2-(hydroxymethyl)pyrrolidin-1-yl)ethyl)-5-methylisoquinolin-1(2H)-oneYield 12.1%

Procedure

By the reaction in the same manner as in Example 1a, using N,N-diethyl-2,3-dimethylbenzamide (81.4 g) and (R)-3-(2-hydroxymethylpyrrolidin-1-yl)propionitrile (55.6 g), (R)-3-[2-(2-hydroxymethylpyrrolidin-1-yl)ethyl]-5-methyl-2H-isoquinolin-1-one (12.5 g) was obtained.

Workup

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

Sources & evidence

ORD record
ord-0ff516e1eef5422eba50620375ab4766
Source dataset
uspto-grants-2008_12
Patent number
US07459465B2

Reaction notes

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