Diisopropylamine → 1-(4-Ethoxycarbonyl-butyl)-indan-1-carboxylic acid methyl ester

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Reaction Steps

Indan-1-carboxylic acid methyl ester (17.6 g, 100 mmol) in 100 mL of THF was slowly added to a −60° C. solution of lithium diisopropylamide (from 15.4 mL (110 mmol) of diisopropylamine and 42 mL of 2.5M n-BuLi in hexane) in 200 mL of THF. After 15 min, methyl 5-bromopentanoate (20.5 g, 105 mmol) was added and the mixture was allowed to warm to room temperature and stirred for 12 h. Ether and water were added and the ether layer was separated, washed with water and brine, dried and evaporated. Purification by flash chromatography (10% ethyl acetate/hexane) afforded 15 g of 1-(4-ethoxycarbonyl-butyl)-indan-1-carboxylic acid methyl ester as an oil.

Provenance & Evidence