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

HRID 65055Notes

Reaction equation

HRID 65055 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[C@H:5]([CH3:16])[NH:4]1.C(N(CC)CC)C.[C:24](=[S:26])=[S:25].[CH3:27]I>CS(C)=O>[OH:1][CH2:2][C@H:3]1[CH2:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[C@H:5]([CH3:16])[N:4]1[C:24]([S:26][CH3:27])=[S:25]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 86741002(1RS, 3SR)-trans-3-hydroxymethyl-1-methyl-1,2,3,4-tetrahydro-beta-carboline

Product 1

HCID 86741001Methyl (1RS, 3SR)-trans-3-hydroxymethyl-1-methyl-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-3-hydroxymethyl-1-methyl-1,2,3,4-tetrahydro-β-carboline (1.08 g), triethylamine (1.01 g), CS2 (760 mg), methyl iodide (1.42 g) and dimethylsulfoxide (10 ml), there is prepared the title compound (1.22 g, 79.7%) as colorless needles, m.p. 153°-156° C. (recrystallized from aqueous methanol). NMR (CDCl3, δ): 2.60 (d, J=7.0 Hz, 3H, C1 --CH3), 2.68 (s, 3H, CSSCH3), Mass m/e: 306 (M+), 258 (M+ --CH3SH).

Workup

  1. customis prepared
  2. customthe title compound (1.22 g, 79.7%) as colorless needles, m.p. 153°-156° C. (recrystallized from aqueous methanol)

Sources & evidence

ORD record
ord-3c88501de8434f5898a59c746a53cb26
Source dataset
uspto-grants-1986_09
Patent number
US04612317

Reaction notes

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