Water → Tert-butyl 4-(methylsulfonyloxymethyl)piperidine-1-carboxylate

HRID 715913Notes

Reaction equation

HRID 715913 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.O.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>ClCCl.C(N(CC)CC)C>[CH3:17][S:18]([O:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)(=[O:20])=[O:19]

Participants

6

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 2765838Tert-butyl 4-(methylsulfonyloxymethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate (2.5 g) in dichloromethane (40 ml), triethylamine (2.8 ml) and methanesulfonyl chloride (1.2 ml) were added under ice cooling, and the mixture was stirred at room temperature for 3 hours. Water was added to the reaction solution to separate two layers. Then, the aqueous layer was subjected to extraction with chloroform. The organic layers were combined, washed with saturated saline and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane-ethyl acetate) to obtain the title compound (2.8 g).

Workup

  1. customto separate two layers
  2. extractionThen, the aqueous layer was subjected to extraction with chloroform
  3. washwashed with saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-b30dd5ad0f6b4a178014d6817d7a5514
Source dataset
uspto-grants-2015_11
Patent number
US09187489B2

Reaction notes

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