Methanol → N-(tert-Butoxycarbonyl)-D-prolinol

Participants

Reaction Steps

To a solution of 25.0 g of N-α-t-BOC-D-proline in 250 ml of tetrahydrofuran which is cooled to 0° C. is added dropwise 15 ml of 10M borane-methyl sulfide complex. The reaction is kept at around -20° C. during the addition followed by warming to room temperature and then is gently refluxed for one hour. The mixture is cooled to 0° C., 250 ml of methanol is added carefully and the reaction is evaporated in vacuo to give 23.3 g of a colorless oil which crystallizes on standing to a colorless solid, mp 50°-53° C., [α]D26° =+47°±1 (C=1.162%, methylene chloride).

Provenance & Evidence