HCID 66617615, compound → HCID 58944685, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)cyclopent-2-en-1-one (250. mg, 0.713 mmol) in diethyl ether (10.0 mL) tinder an atmosphere of nitrogen was cooled to −40° C. and a 1.60 M solution of methyllithium in diethyl ether (0.579 mL, 0.926 mmol) was added slowly and the mixture was stirred at −40° C. for 3 h. TLC indicated complete conversion, and the reaction was quenched via addition of saturated aqueous ammonium chloride (5.00 mL), extracted with EtOAc (3×10.0 mL), dried over MgSO4, filtered, and concentrated in vacuo. Silica gel chromatography eluting with a gradient of 0 to 50% EtOAc in hexanes afforded the title compound (190 mg, 73%). Stereochemistry of the product was confirmed using ROESY analysis. LC/MS: Rt=2.55 min, ES+ 367 (AA standard).

Provenance & Evidence