N,N,2,3-tetramethylbenzamide → (R)-3-[3-(2-hydroxymethylpyrrolidin-1-yl)propyl]-5-methyl-2H-isoquinolin-1-one

HRID 1352444Notes

Reaction equation

HRID 1352444 reaction equation
C[N:2]([CH3:13])[C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1[CH3:11].[OH:14][CH2:15][C@H:16]1[CH2:20][CH2:19][CH2:18][N:17]1[CH2:21][CH2:22][CH2:23]C#N>>[OH:14][CH2:15][C@H:16]1[CH2:20][CH2:19][CH2:18][N:17]1[CH2:21][CH2:22][CH2:23][C:13]1[NH:2][C:3](=[O:12])[C:4]2[C:5]([CH:11]=1)=[C:6]([CH3:10])[CH:7]=[CH:8][CH:9]=2

Participants

3

Reactant 2

HCID 22931034N,N,2,3-tetramethylbenzamideHCID 62733483(R)-4-(2-hydroxymethylpyrrolidin-1-yl)butyronitrile

Product 1

HCID 10424887(R)-3-[3-(2-hydroxymethylpyrrolidin-1-yl)propyl]-5-methyl-2H-isoquinolin-1-oneYield 7%

Procedure

By the reaction in the same manner as in Example 1a, using N,N-dimethyl-2,3-dimethylbenzamide (5.8040 g) and (R)-4-(2-hydroxymethylpyrrolidin-1-yl)butyronitrile (2.75 g), (R)-3-[3-(2-hydroxymethylpyrrolidin-1-yl)propyl]-5-methyl-2H-isoquinolin-1-one (344.1 mg) was obtained.

Workup

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

Sources & evidence

ORD record
ord-27313b747dd74d0b9d76e2d19eb25876
Source dataset
uspto-grants-2007_05
Patent number
US07220759B2

Reaction notes

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