Water → 1-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

HRID 336829Notes

Reaction equation

HRID 336829 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24].O>ClCCl.CN(C)C1C=CN=CC=1>[CH3:22][S:23]([O:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]1)(=[O:25])=[O:24]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineYield 100.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To 1 g (4.97 mmol) of tert-butyl 4-hydroxypiperidine-1-carboxylate diluted in 12.5 ml of anhydrous dichloro-methane are added dropwise at 0° C. 718 μl, of triethylamine (4.97 mmol), then 385 μL (4.97 mmol) methanesulfonyl chloride and finally 6 mg (49.6 μmol) of 4-dimethylamino-pyridine (DMAP). The solution is stirred at room temperature for 20 h, then water is added and the product is extracted several times with dichloromethane. The organic phases are combined, dried over magnesium sulfate, and concentrated to yield 1.39 g of tert-butyl 4-(methylsulfonyloxy)piperidine-1-carboxylate in the form of white solid.

Workup

  1. additionare added dropwise at 0° C
  2. extractionthe product is extracted several times with dichloromethane
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3b2167b9617149b4bf164c7c2c019cff
Source dataset
uspto-grants-2014_11
Patent number
US08889711B2

Reaction notes

Loading…