Sodium borohydride → HCID 90424018, compound

Participants

Reaction Conditions

Reaction Steps

Add diisobutylaluminum hydride (1M in hexanes; 21.65 mL; 1.6 equiv; 21.65 mmoles) to a 0° C. solution of (6R)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-5,6-dihydroimidazo[2,1-c][1,4]oxazin-8-one (5.5 g; 1.0 equiv; 13.53 mmoles) in dichloromethane (130 mL). Stir the solution for 15 minutes, then add methanol (100 mL). After 5 minutes, add sodium borohydride (0.307 g; 0.6 equiv; 8.12 mmoles) and maintain the solution at 0° C. for 15 minutes. Add saturated sodium potassium tartrate solution (80 mL) and stir the solution at ambient temperature for 14 hours. Filter the solution and separate the liquid layers. Further extract the aqueous layer with dichloromethane (3×). Wash the combined organic extracts with 50% saturated brine, dry over magnesium sulfate, filter, and concentrate to afford the desired (2R)-1-[tert-butyl(diphenyl)silyl]oxy-3-[2-(hydroxymethyl)imidazol-1-yl]propan-2-ol (5.30 g; 95%). MS (m/z): 411 (M+1).

Provenance & Evidence