Sodium borohydride → HCID 70530323, compound

Participants

Reaction Steps

To a cold (ice bath) suspension of NaBH4 (227 mg, 6 mmol) in tetrahydrofuran (20 ml) was added dropwise a solution of trans 1-(t-butyldimethylsilyl)-3-formyl-4-tritylthio-2-azetidinone (2.0 g, 4.1 mmol) in tetrahydrofuran (5 ml). The reaction mixture was stirred at room temperature for 30 min, then diluted with ethyl acetate and washed successively with cold 1N HCl and brine. The organic layer was dried (MgSO4) and evaporated in vacuo to give the title compound (2.0 g) (quantitative) as an amorphous solid. It was used in the next step without further purification. ir νmax (CDCl3): 1740 cm-1. 1Hmr (CDCl3)δ: 7.25 (15H, m), 4.30 (1H, d, J=2, H-4), 3.28 (1H, dd, J=11, J=3, H-1'), 3.0 (1H, m, H-3), 2.55 (1H, dd, J=11, J=3, H-1'), 2.2 (1H, m, O--H), 0.9 (9H, s, t-Bu and 0.22 ppm (6H, s, CH3).

Provenance & Evidence