Lithium Chloride → HCID 18739113, compound

Participants

Reaction Steps

To a solution of 2-[(3S, 5S)-1-(tert-butoxycarbonyl)-5-(methoxycarbonyl)pyrrolidin-3-ylamino]-N-(3,4-dimethoxylbenzyl)-5-nitrobenzamide (492 mg) in tetrahydrofuran (5 mL) was added lithium chloride (75 mg), and then a solution of sodium borohydride (67 mg) in ethanol (10 mL) at ambient temperature. After stirring for one day, the mixture was evaporated and the residue was partitioned between ethyl acetate and 10% citric acid aqueous solution. The organic layer was separated, washed with water and brine and dried over magnesium sulfate. The residue was subjected to a silica gel column chromatography eluting with a mixture of ethyl acetate and hexane (1:1 to 2:1) to give 2-[(3S,5S)-1-(tert-butoxycarbonyl)-5-(hydroxymethyl)pyrrolidin-3-ylamino]-N-(3,4-dimethoxylbenzyl)-5-nitrobenzamide (399 mg) as pale yellow foams.

Provenance & Evidence