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

HRID 1095172Notes

Reaction equation

HRID 1095172 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 88.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

At 0° C., to a solution of 4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (4 g, 20.20 mmol) and DMAP (3 g, 24 mmol) in DCM (50 mL) was added methanesulfonyl chloride (2.7 g, 24 mmol). After stirred for 2 h, the mixture was filtrated. The filtrate was washed by 0.5N HCl (50 mL), Na2CO3 aqueous solution (1 M, 50 mL) and brine (50 mL), dried over anhydrous Na2SO4, and concentrated to give the title compound as a yellow solid (5 g).

Workup

  1. filtrationthe mixture was filtrated
  2. washThe filtrate was washed by 0.5N HCl (50 mL), Na2CO3 aqueous solution (1 M, 50 mL) and brine (50 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-404b3117365a403b8f37ff5995dd82b6
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

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