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

HRID 65049Notes

Reaction equation

HRID 65049 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.[OH-].[K+].[C:18](=[S:20])=[S:19].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(O)C>[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:18]([S:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[S:19]

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 13375507(3R)-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline

Product 1

HCID 13375521Benzyl (3R)-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioateYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(3R)-3-Hydroxymethyl-1,2,3,4-tetrahydro-β-carboline (1.01 g) is dissolved in 70% ethanol (20 ml), and thereto is added dropwise 2N KOH (2.5 ml) and is further added CS2 (0.30 ml). The mixture is stirred at room temperature for 30 minutes, and thereto is added dropwise benzyl bromide (0.86 g). The mixture is stirred at room temperature for 4 hours and distilled to remove the solvent. The residue is dissolved in ethyl acetate, and the solution is washed with 10% HCl and water in order, dried over sodium sulfate, and distilled to remove the solvent. The residue is purified with silica gel column chromatography (solvent: CHCl3 :methanol=10:1) to give the title compound (1.29 g, 70%) as white powder, [α]D20 -117.3° (c=0.99, methanol). NMR (CDCl3,δ): 4.58 (s, 2H, CSSCH2C6H5), Mass m/e: 368 (M+), 244 (M+ --C6H5CH2SH).

Workup

  1. stirringThe mixture is stirred at room temperature for 4 hours
  2. distillationdistilled
  3. customto remove the solvent
  4. dissolutionThe residue is dissolved in ethyl acetate
  5. washthe solution is washed with 10% HCl and water in order
  6. dry with materialdried over sodium sulfate
  7. distillationdistilled
  8. customto remove the solvent
  9. customThe residue is purified with silica gel column chromatography (solvent: CHCl3 :methanol=10:1)

Sources & evidence

ORD record
ord-14c963f23f394fd4881565acc03dafaf
Source dataset
uspto-grants-1986_09
Patent number
US04612317

Reaction notes

Loading…