Sodium Chloride → (R)-(-)-1-CBZ-3-pyrrolidinol

Participants

Reaction Steps

A solution of 10.2 g (82.6 mmol) of R-3-hydroxypyrrolidine hydrochloride (Chem. Letts., 1966, pp 893-6) in 50 ml of water was cooled to 0° and treated with 22.5 ml (90 mmol) of 4.0N sodium hydroxide. The neutral solution was treated dropwise with 15.6 g (86 mmol) of carbobenzyloxy chloride maintaining the pH at 11.0±0.5 by the dropwise addition of 87 ml of 1.0N sodium hydroxide and the temperature below 5° with a salt-ice bath. When the addition was complete, the mixture was stirred at 5° for two hours and stored at 5° for 18 hours. The reaction mixture was saturated with sodium chloride and extracted with ethyl acetate (2×500 ml). The combined organic layers were washed with 1.0N sodium hydroxide (4×50 ml), water, dried (MgSO4) and evaporated in vacuo to give 17.5 of the title compound.

Provenance & Evidence