Reaction #2146773

Reaction equation

(S)-3-[2-(4-Methoxy-benzyl)-7-methyl-1-oxo-1,2-dihydro-isoquinolin-6-yloxy]-pyrrolidine-1-carboxylic acid tert-butyl ester

trifluoroacetic acid

→

7-Methyl-6-((S)-pyrrolidin-3-yloxy)-2H-isoquinolin-1-one

Yield 87.3%

Conditions

Workup

1. 1
   workup.DISTILLATIONThen the excess trifluoroacetic acid was distilled off in vacuo
2. 2
   workup.ADDITIONthe residue was diluted with 10 ml 1 M hydrochloric acid
3. 3
   WashThe aqueous phase was washed with methylene chloride twice
4. 4
   Otherdried

Procedure

0.54 g (1.2 mmol) (S)-3-[2-(4-Methoxy-benzyl)-7-methyl-1-oxo-1,2-dihydro-isoquinolin-6-yloxy]-pyrrolidine-1-carboxylic acid tert-butyl ester were dissolved in 2.7 g (23 mmol) trifluoroacetic acid. After 1 h at room temperature the mixture was heated for 2 h in a microwave oven at 150° C. Then the excess trifluoroacetic acid was distilled off in vacuo and the residue was diluted with 10 ml 1 M hydrochloric acid. The aqueous phase was washed with methylene chloride twice and then it was freeze dried to give 0.256 g 7-Methyl-6-((S)-pyrrolidin-3-yloxy)-2H-isoquinolin-1-one as the hydrochloride. Rt=0.90 min (Method B). Detected mass: 245.2 (M+H+).

Source