Methyl iodide → Methyl (1RS, 3RS)-cis-1-ethyl-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioate

HRID 65058Notes

Reaction equation

HRID 65058 reaction equation
[CH2:1]([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)[CH3:2].C(N(CC)CC)C.[C:25](=[S:27])=[S:26].[CH3:28]I>O.CO>[CH2:1]([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])[CH3:2]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 86741004(1RS, 3RS)-cis-1-ethyl-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline

Product 1

HCID 86741003Methyl (1RS, 3RS)-cis-1-ethyl-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

In the same manner as described in Example 13 by using (1RS, 3RS)-cis-1-ethyl-3-hydroxymethyl-1,2,3,4-tetrahydro-β-carboline (1.04 g), triethylamine (2.73 g), CS2 (2.05 g), methyl iodide (3.84 g), methanol (30 ml) and water (3 ml), there is prepared the title compound (940 mg, 65%) as colorless prisms, m.p. 177°-180° C. (recrystallized from ether). NMR (CDCl3, δ): 1.34 (t, J=7.0 Hz, 3H, C1 --CH2CH3), 2.70 (s, 3H, CSSCH3), Mass m/e: 320 (M+), 272 (M+ --CH3SH).

Workup

  1. customis prepared
  2. customthe title compound (940 mg, 65%) as colorless prisms, m.p. 177°-180° C. (recrystallized from ether)

Sources & evidence

ORD record
ord-c68f665f7f4c4abbb892f55780f8d7d1
Source dataset
uspto-grants-1986_09
Patent number
US04612317

Reaction notes

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