Diisobutylaluminum hydride → Tert-butyl (1r)-1-formyl-2-(phenylthio)ethylcarbamate

Participants

Reaction Steps

A solution of Example 133A (8.1 g, 26.0 mmol) in dichloromethane at −78° C. was treated with 1M DIBAL-H in dichloromethane (52 mL, 52 mmol), stirred for 3 hours, quenched with methanol (20 mL), and poured into saturated NaH2PO4. The mixture was extracted with ethyl acetate (3×300 mL), and the combined extracts were dried (Na2SO4), filtered, concentrated, and purified by flash column chromatography on silica gel with 30% ethyl acetate/hexanes to provide the desired product. MS (ESI(−)) m/e 280 (M−H)−.

Provenance & Evidence