Water → Aspidospermidine-3-carboxylic acid, 2,3-didehydro-1-methyl-, methyl ester, (5alpha,12beta,19alpha)-

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Reaction Steps

A solution of 34 mg (0.1 m mol) of ±vincadifformine in 1 ml of DMF was added at 20° C. to a mixture of 10 mg (0.2 m mol) of 50% NaH-mineral oil in 1 ml of DMF. After 20 min 20 μL (0.3 m mol) of methyl iodide was added to the brown solution. After 10 min 5 ml of water was added resulting in deposition of a gummy product. Decantation of the solvent, addition of ether, filtration of the ether solution through phase separating paper and concentration under vacuum gave 30 mg (85%) of minovine which showed no indolic NH singlet at δ 8.9 and the presence of the N-CH3 singlet at 3.24, integrating for 3 protons. A picrate was prepared with mp 194°-197° C., regeneration of the free base gave minovine, mp 119°-121° C., reported 120°-122° C.8MS (80eV) m/e (vel. intensity %): 124 (100), 168 (7), 228 (4) 267 (7), 352 (55) M+.

Provenance & Evidence