Lawesson's reagent → 1,2,3,4-Tetrahydro-6-methoxy-2-[[1-(t-butoxycarbonyl)-4-piperidinyl]methyl]cyclopent[b]indol-3-thione

HRID 22291Notes

Reaction equation

HRID 22291 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[CH3:23][O:24][C:25]1[CH:26]=[CH:27][C:28]2[C:29]3[CH2:36][CH:35]([CH2:37][CH:38]4[CH2:43][CH2:42][N:41]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:40][CH2:39]4)[C:34](=O)[C:30]=3[NH:31][C:32]=2[CH:33]=1>C1(C)C=CC=CC=1>[CH3:23][O:24][C:25]1[CH:26]=[CH:27][C:28]2[C:29]3[CH2:36][CH:35]([CH2:37][CH:38]4[CH2:43][CH2:42][N:41]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:40][CH2:39]4)[C:34](=[S:10])[C:30]=3[NH:31][C:32]=2[CH:33]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 199278491,2,3,4-Tetrahydro-6-methoxy-2-[[1-(t-butoxycarbonyl)-4-piperidinyl]methyl]cyclopent[b]indol-3-one

Product 1

HCID 544707021,2,3,4-Tetrahydro-6-methoxy-2-[[1-(t-butoxycarbonyl)-4-piperidinyl]methyl]cyclopent[b]indol-3-thioneYield 112.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Lawesson's reagent (244 mg, 0.60 mmol) was added to a mixture of the title compound of Example 60 (400 mg, 1.01 mmol) in toluene and the resulting mixture was heated to 80° C. for 15 minutes. The reaction mixture was concentrated and the residue was purified by chromatography to give the title compound (280 mg, 67%) as an orange solid. Recrystallization from ethyl acetate gave orange crystals, mp. 188°-189° C.; Anal. Calc. for C23H30N2O3S: C, 66.64; H, 7.29; N, 6.76; Found: C, 66.42; H, 7.17; N, 6.59.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by chromatography

Sources & evidence

ORD record
ord-ef4ef30be6ac4b8f8511b1e9e70483d5
Source dataset
uspto-grants-1995_06
Patent number
US05428043

Reaction notes

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