Tetrahydrofuran → HCID 14988545, compound

Participants

Reaction Steps

To a solution of 311 mg. (1 mmole) of 1-benzyloxy-4-benzyloxycarbonylazetidin-2-one in 10 ml. of tetrahydrofuran, cooled in an ice bath, was added a solution of 37 mg. of sodium borohydride in 3 ml. of water. The solution was stirred at ice bath temperature for one hour and was then poured into a separatory funnel containing 25 ml. of ethyl acetate, 25 ml. of water and 2 ml. of acetic acid. After shaking, the layers were separated and the aqueous layer was extracted twice with 25 ml. portions of ethyl acetate. These two extracts were combined with the organic layer. The organic layer was washed twice with 15 ml. portions of 5% aqueous sodium bicarbonate and 15 ml. of brine and was dried over sodium sulfate, filtered and evaporated to give the product as a crude oil. The oil was chromatographed on silica gel with gradient elution (30% ethyl acetate -70% hexanes to 100% ethyl acetate) The fraction containing the purified product (Rf=0.15, silica gel thin layer in 1:1 ethyl acetate-hexanes) was evaporated to yield 121 mg. (61% yield) of the product as an oil.

Provenance & Evidence