Benzyl Alcohol → HCID 57152973, compound

Participants

Reaction Conditions

Reaction Steps

Benzyl alcohol (347 ml) was added to a suspension of sodium hydride (60% dispersion in oil, 89.6 g) in DMI (2.0 l), and the mixture was stirred at 60° C. for 1 hour. A solution of (S)-1-(tert-butoxycarbonyl)-2-(1,2-epoxyethyl)pyrrolidine (478.4 g) obtained in Example 4-a), in DMI (150 ml) was dropwise added, and the mixture was stirred at said temperature for 2 hours. The reaction mixture was poured into a saturated aqueous solution of potassium hydrogensulfate and the mixture was extracted with toluene. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated. The residue (547.9 g) was dissolved in ethanol (3.0 l) and a 30% aqueous solution (1 l) of potassium hydroxide was added. The mixture was stirred at 76° C. for 3 hours. The reaction mixture was concentrated, acidified with 1.2N hydrochloric acid and washed with ethyl acetate. The aqueous layer was made basic with 10% sodium hydroxide and extracted with methylene chloride. The extract was dried over anhydrous sodium sulfate, and concentrated to give the title compound (178.2 g).

Provenance & Evidence