(3R)-1-[(tert-butoxy)carbonyl]pyrrolidine-3-carboxylic acid → (3R)-1-tert-butoxycarbonyl-N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutyl pyrrolidine-3-carboxamide

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Reaction Steps

A mixture of N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-2-methylpropan-1-amine (1,594 mg), (R)-Pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 1,270 mg, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1,480 mg), dimethyl aminopyridine (1,030 mg) in 110 ml dichloromethane was stirred at room temperature overnight. After addition of water (75 mL), the mixture was extracted with ethyl acetate (100 mL 3). The organic layer was washed with saturated sodium bicarbonate, water and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The product was purified by column chromatography on silica (33-50% ethyl acetate in hexane) and received as an oil: MS (m+1)=467.3.

Provenance & Evidence