Methanol → HCID 90423990, compound

Participants

Reaction Conditions

Reaction Steps

Add diisobutylaluminum hydride (35 mL; 1M in hexanes; 1.5 equiv; 35 mmoles) to a 0° C. solution of 6-[[tert-butyl(diphenyl)silyl]oxymethyl]-5,6-dihydroimidazo[2,1-c][1,4]oxazin-8-one (9.48 g; 1.0 equiv; 23.32 mmoles) in dichloromethane (200 mL). Stir the solution for 15 minutes, then add methanol (150 mL). After 5 minutes, add sodium borohydride (0.176 g; 0.2 equiv; 4.66 mmoles) and maintain the solution at 0° C. for 15 minutes. Add saturate sodium potassium tartrate (50 mL) and stir the solution at ambient temperature for 20 minutes. Concentrate the solution to ˜100 mL, add water and dichloromethane (100 mL each), and separate the layers. Further extract the aqueous layer with dichloromethane (5×). Dry the combined organic extracts over magnesium sulfate, filter, and concentrate to afford the desired 1-[tert-butyl(diphenyl)silyl]oxy-3-[2-(hydroxymethyl)imidazol-1-yl]propan-2-ol (9.40 g; 98%). MS (m/z): 411 (M+1).

Provenance & Evidence