Water → Aspidospermidine-3-carboxylic acid, 2,3-didehydro-1-methyl-, methyl ester, (5alpha,12beta,19alpha)-
Reaction equation
[CH3:1][CH2:2][C@:3]12[CH2:21][C:20]([C:22]([O:24][CH3:25])=[O:23])=[C:19]3[C@@:9]4([C:12]5[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=5[NH:18]3)[CH2:10][CH2:11][N:7]([C@@H:8]14)[CH2:6][CH2:5][CH2:4]2.[H-].[Na+].[CH3:28]I.O>CN(C=O)C.CCOCC>[CH3:1][CH2:2][C:3]12[CH2:21][C:20]([C:22]([O:24][CH3:25])=[O:23])=[C:19]3[C:9]4([C:12]5[C:17]([N:18]3[CH3:28])=[CH:16][CH:15]=[CH:14][CH:13]=5)[CH2:10][CH2:11][N:7]([CH:8]14)[CH2:6][CH2:5][CH2:4]2Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
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+.
Workup
- customresulting in deposition of a gummy product
- customseparating
- concentrationpaper and concentration under vacuum
Sources & evidence
- ORD record
- ord-1ab2559bd4724568ac821b2f6c1f5130
- Source dataset
- uspto-grants-1980_09
- Patent number
- US04220774
Reaction notes
Loading…