4-(Dimethylamino)Benzaldehyde → 2,2-Dimethyl-3alpha-cyano-6alpha-(p-dimethylamino-alpha-hydroxybenzyl)penam

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Reaction Steps

A solution of 100 mg 2,2-dimethyl-3α-cyano-6α-bromopenam in 40 ml dry tetrahydrofuran is stirred with 60 mg p-dimethylaminobenzaldehyde and 500 mg zinc for about 12 hours at room temperature. The reaction mixture is then diluted in ethyl acetate, washed with aqueous sodium chloride and dried over anhydrous sodium sulfate. Chromatography of the mixture on silica gel affords, in 11:1 ratio, 2,2-dimethyl-3α-cyano-6α-(p-dimethylamino-α-hydroxybenzyl)penam and 2,2-dimethyl-3α-cyano-6β-(p-dimethylamino-α-hydroxybenzyl)penam. The 6α-compound has the following formula: ##STR39## Utilizing 7α-bromo-4-cyano-3-cephem in the above procedure similarly affords 7α-(p-dimethylamino-α-hydroxybenzyl)-4-cyano-3-cephem.

Provenance & Evidence