Methyl iodide → Methyl (1R, 3R)-3-hydroxymethyl-1-methyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioate

HRID 65054Notes

Reaction equation

HRID 65054 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]I>CO.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[C@@H:5]([CH3:16])[N:4]1[C:24]([S:26][CH3:27])=[S:25]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 13375563(1R, 3R)-3-hydroxymethyl-1-methyl-1,2,3,4-tetrahydro-beta-carboline

Product 1

HCID 13375531Methyl (1R, 3R)-3-hydroxymethyl-1-methyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioateYield 69%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

In the same manner as described in Example 13 by using (1R, 3R)-3-hydroxymethyl-1-methyl-1,2,3,4-tetrahydro-β-carboline (4.32 g), triethylamine (4.04 g), CS2 (3.04 g), methyl iodide (5.68 g) and 80% ethanol (150 ml), there is prepared the title compound (4.22 g, 69%) as white powder, [α]D20 -205.4° (c=1.0, methanol). NMR (CDCl3, δ): 1.66 (d, J=6.7 Hz, 3H, C1 --CH3), 2.70 (s, 3H, CSSCH3), Mass m/e: 306 (M+), 258 (M+ --CH3SH).

Sources & evidence

ORD record
ord-27158436d0ae4299954b0349880fcd1e
Source dataset
uspto-grants-1986_09
Patent number
US04612317

Reaction notes

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