Carbon Disulfide → Butyl (3S)-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioate

HRID 65048Notes

Reaction equation

HRID 65048 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[CH2:5][NH:4]1.C(N(CC)CC)C.[C:23](=[S:25])=[S:24].[CH2:26](I)[CH2:27][CH2:28][CH3:29]>O.CO>[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[CH2:5][N:4]1[C:23]([S:25][CH2:26][CH2:27][CH2:28][CH3:29])=[S:24]

Participants

7

Reactant 4

HCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 10962Butyl iodideHCID 13375506(3S)-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline

Product 1

HCID 13375519Butyl (3S)-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 2 by using (3S)-3-hydroxymethyl-1,2,3,4-tetrahydro-β-carboline (2.02 g), triethylamine (1.52 g), CS2 (1.14 g), n-butyl iodide (2.97 g), methanol (25 ml) and water (5 ml), there is prepared the title compound (2.0 g, 60%) as colorless needles, m.p. 60°-63° C. (recrystallized from ethanol), [α]D20 +133.6° (c=1.0, methanol). NMR (CDCl3, δ): 0.93 (m, 3H, CSS(CH2)3CH3), Mass m/e: 334 (M+), 244 (M+ -n-thiobutanol).

Workup

  1. customis prepared
  2. customthe title compound (2.0 g, 60%) as colorless needles, m.p. 60°-63° C. (recrystallized from ethanol), [α]D20 +133.6° (c=1.0, methanol)

Sources & evidence

ORD record
ord-060e4852e59740c19f7ee4d0315a8a32
Source dataset
uspto-grants-1986_09
Patent number
US04612317

Reaction notes

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