Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → (S)-tert-butyl 1-(1-fluorocyclohexyl)-3-hydroxypropan-2-ylcarbamate

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Reaction Steps

(S)-tert-butyl 4-((1-fluorocyclohexyl)methyl)-2,2-dimethyloxazolidine-3-carboxylate (1.1 g, 3.50 mmol, 1.0 equiv) was dissolved in methanol (30 mL). To this mixture was added camphorsulfonic acid (202 mg, 0.875 mmol, 0.5 equiv) and the solution was stirred at rt for 3 h. After this time the starting material was consumed. Satd aq NaHCO3 was added and the methanol was removed in vacuo. The aqueous residue was extracted with EtOAc (3×10 mL) and the combined organic extracts were washed with brine, dried over Na2SO4, filtered and evaporated. Flash chromatography on silica, eluting with 0-47% EtOAc in hexanes, afforded (S)-tert-butyl 1-(1-fluorocyclohexyl)-3-hydroxypropan-2-ylcarbamate (275 mg).

Provenance & Evidence