Sodium borohydride → HCID 58767572, compound

Participants

Reaction Conditions

Reaction Steps

1-(Cyano-dimethyl-methyl)-1H-indole-2,6-dicarboxylic acid diethyl ester (238, 0.725 mmol) was suspended in 3 mL of MeOH and 2 mL of THF, and 188 mg (1.45 mmol) of CoCl2 was added. While the mixture was stirred in a 0° C. bath, 274 mg (7.25 mmol) of NaBH4 was carefully added in small portions. The cold bath was removed and the mixture was stirred for 30 min. The vessel was sealed and heated to 60° C. with stirring for 4 h. The mixture was cooled and partitioned between EtOAc and saturated aqueous NaHCO3. The organic phase was then washed with 1 M NaHSO4 and brine, dried with Na2SO4, filtered, and concentrated. The residue was chromatographed (1-5% MeOH in CH2Cl2) to provided 65 mg of 4,4-dimethyl-1-oxo-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole-7-carboxylic acid ethyl ester. ESI-MS m/z 287 [M+H]+.

Provenance & Evidence