Methyl vinyl sulfone → tert-Butyl 4-(2-(methylsulfonyl)ethyl)piperazine-1-carboxylate

HRID 2105869Notes

Reaction equation

HRID 2105869 reaction equation
[CH:1]([S:3]([CH3:6])(=[O:5])=[O:4])=[CH2:2].[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]>CO>[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][N:17]([CH2:2][CH2:1][S:3]([CH3:6])(=[O:5])=[O:4])[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:8])[CH3:9]

Participants

4

Reactant 2

HCID 19354Methyl vinyl sulfoneHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 66649624tert-Butyl 4-(2-(methylsulfonyl)ethyl)piperazine-1-carboxylateYield 97.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl vinyl sulfone (1.8 mL, 20.1 mmol) was added to a solution of 1-(tert-butyloxycarbonyl)piperazine (1.50 g, 8 mmol) in methanol (84 mL). The reaction mixture was stirred at room temperature for 4 h and concentrated to a white solid. Purification of the solid by flash column chromatography (silica gel, eluting with 1-5% methanol in methylene chloride) gave 1-tert-butyloxycarbonyl-4-(2-methanesulfonylethyl)piperazine as a white solid (2.29 g, 95%).

Workup

  1. concentrationconcentrated to a white solid
  2. customPurification of the solid
  3. washby flash column chromatography (silica gel, eluting with 1-5% methanol in methylene chloride)

Sources & evidence

ORD record
ord-9cc3b991323141eba081f88ed43d0592
Source dataset
uspto-grants-2009_08
Patent number
US07579368B2

Reaction notes

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