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

HRID 65068

Reaction equation

HRID 65068 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](Br)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]>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[CH2:5][N:4]1[C:23]([S:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[S:24]

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 81731-BromodecaneHCID 8471TriethylamineHCID 13375506(3S)-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline

Product 1

HCID 13392983n-Decyl (3S)-3-hydroxymethyl-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 29 by using (3S)-3-hydroxymethyl-1,2,3,4-tetrahydro-β-carboline (2.02 g), triethylamine (1.67 ml), CS2 (0.72 ml), n-decyl bromide (2.65 g) and dimethylsulfoxide (10 ml), there is prepared the title compound (2,48 g, 59%) as colorless needles, m.p. 115°-118° C. (recrystallized from ether-n-hexane), [α]D20 +113.0° (c=1.0, methanol); NMR (CDCl3, δ): 0.95 (m, 3H, --CH3); Mass m/e: 418 (M+), 244 (M+ --C10H21SH).

Workup

  1. customis prepared
  2. customthe title compound (2,48 g, 59%) as colorless needles, m.p. 115°-118° C. (recrystallized from ether-n-hexane), [α]D20 +113.0° (c=1.0, methanol)

Sources & evidence

ORD record
ord-fe5e6cce12ce49b6a922bf6da1fef0e1
Source dataset
uspto-grants-1986_09
Patent number
US04612317

Linked notes

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