Methyl iodide → Ethyl (3R)-2-[(methylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylate

HRID 1249069Notes

Reaction equation

HRID 1249069 reaction equation
[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][C@H:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[NH:2]1.C(N(CC)CC)C.[C:26](=[S:28])=[S:27].[CH3:29]I>C(O)C>[CH3:29][S:27][C:26]([N:2]1[C@@H:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:4][C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[NH:12][C:13]=2[CH2:1]1)=[S:28]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 7223904ethyl (3R)-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylate

Product 1

HCID 13561982Ethyl (3R)-2-[(methylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In the same manner as described in Example 53, ethyl (3R)-1,2,3,4-tetrahydro-β-carboline-3-carboxylate (224 mg), triethylamine (120 mg), carbon disulfide (0.08 ml), ethanol (25 ml) and methyl iodide (0.08 ml) are reacted and treated. The product is crystallized from ether to give the title compound (140 mg) as colorless prisms, m.p. 139°-141° C.

Workup

  1. customare reacted
  2. additiontreated
  3. customThe product is crystallized from ether

Sources & evidence

ORD record
ord-d3c976da8dd840d1903f027a69d3381b
Source dataset
uspto-grants-1986_12
Patent number
US04628057

Reaction notes

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