Hydrochloric Acid → N-Tosylhydroxy-L-prolinol

Participants

Reaction Conditions

Reaction Steps

(2S,4R)-1-(4-toluenesulfonyl)-2-hydroxymethyl-4-hydroxy pyrrolidine. To a solution of N-tosylhydroxy-L-proline methyl ester (62.20 g, 0.21 mole) in THF (600 mL) at 0° C. was added LiBH4 (15.8 g, 0.73 mole) in small portions. The reaction mixture was stirred at 0° C. for 1 h and allowed to stand at 23° C. for 18 h. The reaction mixture was cooled to -20° C., made neutral with 6N HCl and concentrated under reduced pressure. The residue was treated with water (550 ml) and extracted with EtOAc (4×300 mL). The combined organic extracts were washed with H2O, dried over MgSO4, filtered and concentrated under reduced pressure to give N-tosylhydroxy-L-prolinol as a white solid (50.56 g, 88.8%) which was used in the next step without further purification.

Provenance & Evidence