Triethylamine → tert-Butyl 4-(2-((methanesulfonyl)oxy)ethyl)piperidine-1-carboxylate

HRID 1193333Notes

Reaction equation

HRID 1193333 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1.C(N(CC)CC)C>ClCCl>[CH3:1][S:2]([O:6][CH2:7][CH2:8][CH:9]1[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH2:14]1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 8541401-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidine

Product 1

HCID 15229596tert-Butyl 4-(2-((methanesulfonyl)oxy)ethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methanesulfonic acid chloride (0.41 ml, 6.5 mmol, 1.5 eq) was added to an ice-cooled (0° C.) solution of tert-butyl 4-(2-hydroxyethyl)piperidine-1-carboxylate (1.0 g, 4.37 mmol, 1 eq) and triethylamine (1.2 ml, 8.7 mmol, 2.0 eq) in dichloromethane (10 ml), and stirring was carried out for 1 h at RT. After monitoring by thin-layer chromatography, the reaction mixture was diluted with dichloromethane (75 ml), washed with water and sat. NaCl solution (in each case 30 ml), dried over sodium sulfate and concentrated under reduced pressure. A yellow oil was obtained, which was used in the next step without being purified further.

Workup

  1. washwashed with water and sat. NaCl solution (in each case 30 ml),
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customA yellow oil was obtained
  5. customwithout being purified further

Sources & evidence

ORD record
ord-c47dd4097ef9454ba35328ee6602e633
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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