Chlorotrimethylsilane → HCID 57941061, compound

Participants

Reaction Conditions

Reaction Steps

To (S,S)-bis α-methyl benzylamine (9 g, 40 mmol) in THF (200 mL) under argon was added dibutyl magnesium in heptane (20 mL, 1M) and the mixture heated to reflux. After 1.5 hours, the mixture was cooled to −78° C. and trimethylsilyl chloride (10.1 mL) and N,N-dimethylpropyleneurea (1.2 mL) added dropwise. After a further 20 minutes ethyl-4-oxocyclohexane carboxylate (2.87 mL, 18 mmol) was added dropwise. The reaction was stirred at −78° C. for 16 hours, then saturated sodium hydrogen carbonate (100 mL), water (100 mL) and hexane (200 mL) were added. The organic soluble material was purified by chromatography on silica gel eluting with 0-5% diethyl ether in hexane to give an oil (3.5 g, 80%).

Provenance & Evidence