Water → HCID 59536617, compound

Participants

Reaction Conditions

Reaction Steps

Add palladium (II) acetate (50.0 mg; 0.22 mmol) to a stirred solution of (3S)-tert-butyl 3-(1-hydroxybut-3-enyl)pyrrolidine-1-carboxylate (S-mix) (3.0 g, 12.43 mmol) and freshly prepared diazomethane (50 mL, about 23.8 mmol in diethyl ether) in THF (20 mL) under nitrogen at 0° C. (Caution: vigorous gas evolution). Stir at 0° C. for 10 minutes. Warm to room temperature, pour into water and extract with ethyl acetate (3×). Wash the combined organics with water and brine. Dry (MgSO4), filter and concentrate under reduced pressure. Subject the residue to silica gel chromatography, eluting with 0-100% ethyl acetate in hexane to afford 2.9 g (91%) of the title compound. MS (m/z)=200.0 (M−55)

Provenance & Evidence