Sodium Bicarbonate → HCID 68819514, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-(1-phenyl-ethylamino)-7-aza-bicyclo[2.2.1]hept-2-ene-2,7-dicarboxylic acid 7-tert-butyl ester 2-methyl ester (0.3 g, 0.81 mmol) in acetic acid-acetonitrile (1:1, 20 mL) was treated with sodium triacetoxyborohydride (0.19 g, 0.89 mmol), stirred for 5 h at 0° C. and then neutralized with saturated aqueous sodium bicarbonate (5 mL). The organic layer was washed with brine (3×20 mL), then dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by Biotage Flash 40S chromatography, eluting with 2:1 ethyl acetate-hexanes, to provide 3-(1-phenyl-ethylamino)-7-aza-bicyclo[2.2.1]heptane-2,7-dicarboxylic acid 7-tert-butyl ester 2-methyl ester as a 3:1 mixture of diastereomers (0.28 g, 93%). MS: 375 (M+H)+.

Provenance & Evidence