Sodium Hydroxide → HCID 86617384, compound

Participants

Reaction Steps

A solution of 3,5-dichlorobenzaldehyde (0.79 g, 4.5 mmol, 3 eq) in 1,2-dichloroethane (2 ml) is added to a solution of tert-butyl (2S)-2-[(isobutylamino)methyl]pyrrolidine-1-carboxylate (0.38 g, 1.5 mmol, 1 eq) in 1,2-dichloroethane (8 ml) followed by a solution of sodium triacetoxyborohydride (0.95 g, 4.5 mmol, 3 eq) in DMF (2 ml). After 16 hrs water (5 ml) followed by 2N aqueous sodium hydroxide (5 ml) is added. The biphasic mixture is passed through a hydrophobic frit to separate the organic layer. Methanol is added to the organic layer and the solution is loaded onto a SCX-2 (10 g) column. The column is washed with methanol (50 ml) and then the basic material is eluted with 2M ammonia in methanol (50 ml). The solvent is removed in vacuo to give the tert-butyl (2S)-2-{[(3,5-dichlorobenzyl)(isobutyl)amino]methyl}pyrrolidine-1-carboxylate (0.61 g, 98%). LCMS: Rt=4.17 (6 min method) [M+H]=415.4.

Provenance & Evidence