Methyl iodide → HCID 86741011, compound

HRID 65063Notes

Reaction equation

HRID 65063 reaction equation
[CH:1]1([C@H:7]2[C:19]3[NH:18][C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:11]=3[CH2:10][C@@H:9]([CH2:20][OH:21])[NH:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:29](=[S:31])=[S:30].[CH3:32]I>CS(C)=O>[CH:1]1([C@H:7]2[C:19]3[NH:18][C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:11]=3[CH2:10][C@@H:9]([CH2:20][OH:21])[N:8]2[C:29]([S:31][CH3:32])=[S:30])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 86741012(1RS, 3RS)-cis-1-cyclohexyl-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline

Product 1

HCID 86741011HCID 86741011, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In the same manner as described in Example 13 by using (1RS, 3RS)-cis-1-cyclohexyl-3-hydroxymethyl-1,2,3,4-tetrahydro-β-carboline (569 mg) [J.A.C.S. 102, 6976 (1980)], triethylamine (405 mg), CS2 (304 mg), methyl iodide (568 mg) and dimethylsulfoxide (5 ml), there is prepared the title compound (490 mg, 65%) as white powder. NMR (CDCl3, δ): 2.63 (s, 3H, CSSCH3), Mass m/e: 374 (M+), 326 (M+ --CH3SH).

Sources & evidence

ORD record
ord-187571651c6748f396aaf84931ea20be
Source dataset
uspto-grants-1986_09
Patent number
US04612317

Reaction notes

Loading…