Acetic Acid → HCID 67418881, compound

Participants

Reaction Steps

A solution of phenylmethyl 4-oxo-1-piperidinecarboxylate (1 g, 4.29 mmol) and (3S)-3-pyrrolidinol (0.411 g, 4.72 mmol) in 1,2-dichloroethane (14.29 mL) was treated at room temperature under air with sodium triacetoxyborohydride (1.363 g, 6.43 mmol) and glacial acetic acid (0.245 mL, 4.29 mmol). After 16 h, the mixture was diluted with 1N NaOH (75 mL) and extracted with methylene chloride (3×75 mL). The combined organic extracts were washed with brine (1×75 mL), dried over Na2SO4, filtered, and concentrated in vacuo to afford phenylmethyl 4-[(3S)-3-hydroxy-1-pyrrolidinyl]-1-piperidinecarboxylate (1.35 g, 98% yield). This material was used in the next step without further purification. MS (m/z) 305.0 (M+H+).

Provenance & Evidence