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

HRID 65046Notes

Reaction equation

HRID 65046 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].[CH3:26]I>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:23]([S:25][CH3:26])=[S:24]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 13375507(3R)-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline

Product 1

HCID 13375509Methyl (3R)-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In the same manner as described in Example 2 by using (3R)-3-hydroxymethyl-1,2,3,4-tetrahydro-β-carboline (22.58 g), triethylamine (15.7 ml), CS2 (6.93 ml), methyl iodide (7.16 ml) and 70% ethanol (340 ml), there is prepared the title compound (28.7 g, 88%) as colorless needles, m.p. 106°-108° C. (recrystallized from aqueous ethanol), [α]D20 -158.6° (c=1.0, methanol). NMR (CDCl3, δ): 2.67 (s, 3H, CSSCH3), Mass m/e: 292 (M+), 244 (M+ --CH3SH).

Workup

  1. customis prepared
  2. customthe title compound (28.7 g, 88%) as colorless needles, m.p. 106°-108° C. (recrystallized from aqueous ethanol), [α]D20 -158.6° (c=1.0, methanol)

Sources & evidence

ORD record
ord-03a996511c5243199d63e38befa43ae4
Source dataset
uspto-grants-1986_09
Patent number
US04612317

Reaction notes

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