Hydrochloric Acid → Tert-butyl[(1s,2s)-1-{[(3s)-3-fluoropyrrolidin-1-yl]carbonyl}-2-(4-hydroxyphenyl)propyl]carbamate

Participants

Reaction Steps

To a solution of the material from Step A (0.5 g, 1.0 mmol) in THF (10 mL) at 0° C. was added sequentially 30% hydrogen peroxide (0.18 mL, 1.5 mmol) and 3N aqueous sodium hydroxide (0.35 g, 1.0 mmol). After 2 h at this temperature water (30 mL) was added, and the resulting solution was adjusted to pH 5 by the addition of 1N hydrochloric acid. The mixture was extracted with ethyl acetate, and the combined extracts were washed with saturated sodium thiosulfate until the organic phase showed a negative peroxide test. The combined organics were washed with brine, dried (magnesium sulfate), and concentrated in vacuo. The residue was purified by silica gel chromatography (50% ethyl acetate in hexane) to give the title compound as a white foam. LC/MS 389.3 (M+Na).

Provenance & Evidence