Methyl iodide → Methyl (1RS, 3SR)-trans-1,3-dihydroxymethyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioate

HRID 65062Notes

Reaction equation

HRID 65062 reaction equation
[OH:1][CH2:2][C@H:3]1[C:15]2[NH:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]=2[CH2:6][C@H:5]([CH2:16][OH:17])[NH:4]1.C(N(CC)CC)C.[C:25](=[S:27])=[S:26].[CH3:28]I>CS(C)=O>[OH:1][CH2:2][C@H:3]1[C:15]2[NH:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]=2[CH2:6][C@H:5]([CH2:16][OH:17])[N:4]1[C:25]([S:27][CH3:28])=[S:26]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 86741010(1RS, 3SR)-trans-1,3-dihydroxymethyl-1,2,3,4-tetrahydro-beta-carboline

Product 1

HCID 86741009Methyl (1RS, 3SR)-trans-1,3-dihydroxymethyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In the same manner as described in Example 13 by using (1RS, 3SR)-trans-1,3-dihydroxymethyl-1,2,3,4-tetrahydro-β-carboline (0.65 g), triethylamine (0.79 ml), CS2 (0.34 ml), methyl iodide (0.35 ml) and dimethylsulfoxide (6 ml), there is prepared the title compound (350 mg, 39%) as colorless needles, m.p. 179°-180° C. (recrystallized from water-ethanol). NMR (CDCl3 -DMSO-d6, δ): 2.66 (s, 3H, CSSCH3), Mass m/e: 304 (M+ --H2O), 274 (M+ --CH3SH).

Workup

  1. customis prepared
  2. customthe title compound (350 mg, 39%) as colorless needles, m.p. 179°-180° C. (recrystallized from water-ethanol)

Sources & evidence

ORD record
ord-b894784734034d4293e519a666e69275
Source dataset
uspto-grants-1986_09
Patent number
US04612317

Reaction notes

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