Sodium Bicarbonate → HCID 135833322, compound

Participants

Reaction Conditions

Reaction Steps

A solution of titanium tetrachloride (6.3 g) in dichloromethane (10 ml) was added dropwise to a solution of the compound (3.8 g) obtained in Example 23B in dichloromethane (75 ml) under ice-cooling, and the mixture was stirred at 0° C. for 1.5 hours. The reaction mixture was poured over ice-aqueous saturated solution of sodium bicarbonate and the insoluble was filtered off, the organic layer was washed with water, dried (MgSO4) and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (7:3, v/v) to yield 7-benzyl-3-chloro-4-(4-hydroxy-3-methoxyphenyl)-2-(2-oxo-1-pyrrolidinylmethyl)-5,6,7,8-tetrahydrothieno[2,3-b:5,4-c']dipyridine (0.89 g, 25%), which was then recrystallized as colorless prismatic crystals having a melting point of 190 to 191° C.

Provenance & Evidence