Dimethyl Sulfate → HCID 57546217, compound

HRID 913902Notes

Reaction equation

HRID 913902 reaction equation
[C:1]1([C:7]2([CH2:20][O:21][CH2:22][C:23]3[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[C:28]4[C:24]=3[CH:25]=[CH:26][NH:27]4)[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:36]C(C)([O-])C.[K+].S(OC)(OC)(=O)=O>O1CCCC1>[CH3:36][N:27]1[C:28]2[C:24](=[C:23]([CH2:22][O:21][CH2:20][C:7]3([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:18])([CH3:19])[CH3:17])=[O:14])[CH2:11][CH2:12]3)[CH:31]=[C:30]([C:32]([F:34])([F:35])[F:33])[CH:29]=2)[CH:25]=[CH:26]1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 23665647Potassium tert-butoxideHCID 57546043HCID 57546043, compound

Product 1

HCID 57546217HCID 57546217, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl 4-phenyl-4-(((6-(trifluoromethyl)-1H-indol-4-yl)methoxy)methyl)piperidine-1-carboxylate (59 mg, 0.121 mmol) in tetrahydrofuran (5 ml) at 25° C. was treated with potassium tert-butoxide (13.6 mg, 0.121 mmol) and stirred for 5 minutes. Dimethyl sulfate (0.012 ml, 0.121 mmol) was added, the solution was stirred at 25° C. for 1 h, and then concentrated in vacuo. Column chromatography (ethyl acetate/hexanes gradient elution) afforded 45 mg (90%) as a colorless oil. Mass spec.: 503.17 (MH)+.

Workup

  1. stirringthe solution was stirred at 25° C. for 1 h
  2. concentrationconcentrated in vacuo
  3. washColumn chromatography (ethyl acetate/hexanes gradient elution)
  4. customafforded 45 mg (90%) as a colorless oil

Sources & evidence

ORD record
ord-d7de5f6ee2d04df2b097d03c767638a9
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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