Methanesulfonyl chloride → 1-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

HRID 504463Notes

Reaction equation

HRID 504463 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:15][S:16](Cl)(=[O:18])=[O:17]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][S:16]([CH3:15])(=[O:18])=[O:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineYield 90%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (2 g, 20 mmol) and DMAP (3 g, 24 mmol) in DCM (50 mL) was dropped methanesulfonyl chloride (2.7 g, 24 mmol) in ice bath. The reaction mixture was stirred for 2 h at room temperature. Then the mixture was filtered and washed by 0.5N HCl (50 mL), 1N Na2CO3 (50 mL) and brine (50 mL), dried over anhydrous Na2SO4, concentrated to give title compound as a white solid (Yield: 5 g, 90%).

Workup

  1. filtrationThen the mixture was filtered
  2. washwashed by 0.5N HCl (50 mL), 1N Na2CO3 (50 mL) and brine (50 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ff2861e2b76a4ad7ad37cfea97dfbca1
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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