Salicylic Acid → (3aS-cis)-6-Formyl-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-5-ol salicylate hemihydrate

Participants

Reaction Conditions

Reaction Steps

A solution prepared from 6-formyl-N,N-diethylcarbamate ester of eseroline (960 mg) in ethanol (20 ml) and 10% NaOH (10 ml) was degassed and heated at 45° C. for 30 minutes. The solution was poured into degassed sodium bicarbonate solution (15 ml) and extracted with ethyl acetate (3×150 ml). The ethyl acetate solution was washed with brine (150 ml), dried over MgSO4, and concentrated to an oil. Purification was effected by flash chromatography over silica gel using 1% CH3OH/DCM. The pure product thus obtained weighed 722 mg as an oil. The oil was dissolved in ether (15 ml) and treated with a solution of salicylic acid (405 mg) in ether (20 ml). The crystalline product weighed 1.04 g, mp 156°-157° C.

Provenance & Evidence