Carbon Disulfide → 4-Methoxybenzyl (1RS, 3RS)-cis-3-hydroxymethyl-1-methyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioate

HRID 65075Notes

Reaction equation

HRID 65075 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][O:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33]Cl)=[CH:31][CH:30]=1>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][CH2:33][C:32]1[CH:35]=[CH:36][C:29]([O:28][CH3:27])=[CH:30][CH:31]=1)=[S:25]

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 699934-Methyloxybenzyl chlorideHCID 13375562(1S, 3S)-3-hydroxymethyl-1-methyl-1,2,3,4-tetrahydro-beta-carboline

Product 1

HCID 867410154-Methoxybenzyl (1RS, 3RS)-cis-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 34 by using (1RS, 3RS)-cis-3-hydroxymethyl-1-methyl-1,2,3,4-tetrahydro-β-carboline (2.16 g), triethylamine (1.4 ml), CS2 (0.60 ml), 4-methoxybenzyl chloride (2.01 g) and dimethylsulfoxide (10 ml), there is prepared the title compound (3.0 g, 73%) as colorless needles, m.p. 152°-153° C. (recrystallized from aqueous ethanol), NMR (CDCl3, δ): 3.79 (s, 3H, ##STR21## 4.57 (s, 2H, ##STR22## Mass m/e: 412 (M+), 258 (M+ -- ##STR23##

Workup

  1. customis prepared
  2. customthe title compound (3.0 g, 73%) as colorless needles, m.p. 152°-153° C. (recrystallized from aqueous ethanol), NMR (CDCl3, δ): 3.79 (s, 3H, ##STR21## 4.57 (

Sources & evidence

ORD record
ord-48b76898426d437c94988b58e500b7f0
Source dataset
uspto-grants-1986_09
Patent number
US04612317

Reaction notes

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