Tert-Butylamine → HCID 53746079, compound

Participants

Reaction Conditions

Reaction Steps

2.65 g of N-(benzyloxycarbonyl)-4(R)-hydroxy-L-proline were dissolved in 10 ml of dry tetrahydrofuran and cooled to -10° C. while stirring with a magnetic stirrer. 1.15 g of N-ethylmorpholine were added followed immediately by 1.36 g of isobutyl chloroformate. The mixture was stirred at -10° C. for 30 minutes and then 2.19 g of tert.butylamine were added. Stirring was continued at -10° C. for 1 hour, the mixture was allowed to warm to room temperature during 2 hours and was then left to stand for 2 hours. The solvent was removed by evaporation in a vacuum and the residue was partitioned between ethyl acetate and water. The organic layer was washed with 10% citric acid solution and sodium bicarbonate solution and then dried over sodium sulphate. The solvent was removed by evaporation to give a solid which was triturated with diethyl ether and filtered off. There were obtained 2.23 g of crude product which was recrystallized from ethyl acetate/diethyl ether to give 1.57 g of N2 (benzyloxycarbonyl)-N1 tert.butyl-4(R)-hydroxy-L-prolinamide of melting point 128°-130° C.

Provenance & Evidence