Water → HCID 131723681, compound

Participants

Reaction Steps

2-Chloro-5-formyl-N-(tricyclo [3.3.1.13,7]dec-1-ylmethyl)-benzamide (0.270 g, Example 31a) and 3-amino-1-pyrrolidinecarboxylic acid, 1,1-dimethylethyl ester (0.325 g, Journal of Medicinal Chemistry, 1998, 41(22), 4273-4278) were dissolved in 1,2-dichloroethane (30 ml), under a nitrogen atmosphere. Sodium triacetoxyborohydride (0.24 g) was added and the mixture was stirred for 14 h at room temperature. Water and dichloromethane were added and the layers were partitioned. The organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by HPLC eluting with a gradient of 0-10% of ethanol in dichloromethane, then by chromatography over silica gel eluting with ethyl acetate: iso-hexane (1:1) then ethyl acetate: ethanol (98:2) to give the subtitle compound as a colourless oil (0.158 g).

Provenance & Evidence