Pyridine → tert-Butyl [1-(methanesulfonyl)piperidin-4-yl]carbamate

HRID 538633Notes

Reaction equation

HRID 538633 reaction equation
[C:1]([N:8]1CCC(N)CC1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:15][S:16](Cl)(=[O:18])=[O:17].[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O>[C:4]([O:3][C:1](=[O:2])[NH:8][CH:23]1[CH2:24][CH2:25][N:20]([S:16]([CH3:15])(=[O:18])=[O:17])[CH2:21][CH2:22]1)([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 12682914-Amino-1-Boc-piperidine

Product 1

HCID 25250149tert-Butyl [1-(methanesulfonyl)piperidin-4-yl]carbamateYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.00 g (25.0 mmol) of BOC-4-aminopiperidine are dissolved in pyridine (19.8 mL) and cooled in an ice bath. 2.13 mL (27.5 mmol) of methanesulfonyl chloride are added slowly. The reaction is stirred at RT for 16 h. After diluting with water, the reaction is extracted with DCM. Organic layers are washed with water, dried with MgSO4 and filtered. The solvent is removed under reduced pressure to afford 6.30 g of (1-Methanesulfonyl-piperidin-4-yl)-carbamic acid tert-butyl ester. Yield: 91%; ESI-MS: 279 [M+H]+

Workup

  1. temperaturecooled in an ice bath
  2. extractionthe reaction is extracted with DCM
  3. washOrganic layers are washed with water
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-f075d44756e54d73aeebaab4441009ff
Source dataset
uspto-grants-2014_10
Patent number
US08865744B1

Reaction notes

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