Methanol → HCID 67092835, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (3S,5R)-3-allyl-5-{[benzyloxycarbonyl-((S)-1-tert-butoxycarbonyl-ethyl)-amino]-methyl}-morpholine-4-carboxylic acid tert-butyl ester (4.50 g, 8.68 mmol) in tetrahydrofuran (90 mL) was added 9-borabicyclo[3.3.1]nonane solution (0.5 M in tetrahydrofuran, 36.4 mL, 18.2 mmol) at 0° C., then after 21/2 h another portion of 9-borabicyclo[3.3.1]nonane solution (0.5 M in tetrahydrofuran, 20.8 mL, 10.4 mmol) was added. The reaction mixture was stirred for another 45 min at 0° C., then methanol (80 mL), water (115 mL) and sodium perborate tetrahydrate (37.3 g, 242 mmol) were added. After 90 min the ice bath was removed, then after stirring for 16 h the reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated. Chromatography (SiO2; heptane-ethyl acetate gradient) afforded the title compound (3.76 g, 81%). Colourless gum, MS: 537.5 (M+H)+.

Provenance & Evidence