Methyl iodide → HCID 86741150, compound

HRID 1249060Notes

Reaction equation

HRID 1249060 reaction equation
[CH2:1]([C@H:3]1[C:15]2[NH:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]=2[CH2:6][C@@H:5]([C:16]([OH:18])=[O:17])[NH:4]1)[CH3:2].C(N(CC)CC)C.[C:26](=[S:28])=[S:27].[CH3:29]I>O.CO>[CH2:1]([C@H:3]1[C:15]2[NH:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]=2[CH2:6][C@@H:5]([C:16]([OH:18])=[O:17])[N:4]1[C:26]([S:28][CH3:29])=[S:27])[CH3:2]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 178220(1S,3S)-1-Ethyl-2,3,4,9-tetrahydro-1H-pyrido(3,4-b)indole-3-carboxylic acid

Product 1

HCID 86741150HCID 86741150, compoundYield 52.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

In the same manner as described in Example 43, (1RS,3RS)-cis-1-ethyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (1.22 g), triethylamine (1.21 g), carbon disulfide (456 mg), methyl iodide (852 mg), methanol (30 ml) and water (3 ml) are reacted and treated. The product is recrystallized from aqueous ethanol to give the title compound (880 mg, 52.7%) as colorless prisms, m.p. 198°-200° C.

Workup

  1. customare reacted
  2. additiontreated
  3. customThe product is recrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-856050c2a3374b888053f9d24f0a78cd
Source dataset
uspto-grants-1986_12
Patent number
US04628057

Reaction notes

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