5-(5-Hydroxy-pent-1-ynyl)-indole-1-carboxylic acid tert-butyl ester → 5-(5-Hydroxy-pentyl)-indole-1-carboxylic acid tert-butyl ester

Participants

Reaction Steps

2.85 g (9.5 mmol) 5-(5-Hydroxy-pent-1-ynyl)-indole-1-carboxylic acid tert-butyl ester in 100 ml MeOH were subjected to hydrogenation with 300 mg 10%Pd/C to yield 2.8 g 5-(5-Hydroxy-pentyl)-indole-1-carboxylic acid tert-butyl ester as colorless oil, MS: 303 (M). To the crude material in 60 ml CH2Cl2, 0.87 ml (11 mmol) methanesulfonyl chloride and 3.8 ml (27 mmol) triethyl amine were added at 0° C. The solution was stirred at RT for 1 h.

Provenance & Evidence