HCID 86759216, compound → HCID 70035103, compound

Participants

Reaction Steps

A solution of 4-benzyl-5-(3-ethoxycarbonyl-2-methanesulfonyloxy-propyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (64 g) in dichloromethane (250 ml) was stirred at 15° C. under an atmosphere of nitrogen during the dropwise addition of 1,8-diazobicyclo[5,4,0]undec-7-ene (21.3ml). After 30 minutes, a further portion of 1,8-diazobicyclo[5,4,0]undec-7-ene (9.0ml) was added and the reaction mixture stirred for 1 hour. The solvent was evaporated and the residue dissolved in ethyl acetate, washed sequentially with 2M aqueous hydrochloric acid (500 ml and 250 ml), water, 5% aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride solution, dried (anhydrous magnesium sulfate) and evaporated to afford 4-benzyl-5-(3-ethoxycarbonyl-allyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (49 g, %) as an orange gum. Mass spectrum 404 [M+H]+.

Provenance & Evidence