(3aS)-1-methyl-3,3-diphenyl-hexahydropyrrolo(1,2-c)(1,3,2)oxazaborole → Methyl 4-{2-[(2R)-2((1E,3R,7R)-7-{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxyoct-1-enyl)-5-oxopyrrolidin-1-yl}ethyl}benzoate

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Reaction Steps

To a solution of (S)-2-methyl-CBS-oxazaborolidine (1.0 M in toluene, 0.4 mL, 0.4 mmol) in anhydrous THF (10 mL) at 0° C. was added Borane-THF complex (1.0 M, 0.4 mL, 0.4 mmol) dropwise. The mixture was stirred for 15 minutes. Methyl 4-{2-[(2R)-2((1E,7R)-7-{[tert-butyl(dimethyl)silyl]oxy}-3-oxooct-1-enyl)-5-oxopyrrolidin-1-yl}ethyl}benzoate (200 mg, 0.4 mmol) in THF (1 mL) was added dropwise. The mixture was stirred for 3 hours. The mixture was quenched with addition of 1 mL of the saturated ammonia chloride and was dilute with EtOAc (20 mL). The organic layer was washed with brine (3×5 mL), dried over MgSO4. The residue was used for the next reaction without purification.

Provenance & Evidence