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

HRID 2280633Notes

Reaction equation

HRID 2280633 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]>ClCCl>[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

5

Reactant 3

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

Product 1

HCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineYield 78.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The crude tert-butyl 4-hydroxypiperidine-1-carboxylate 3b (2.01 g, 10 mmol) was dissolved in 30 mL of dichloromethane in an ice bath, followed by addition of triethylamine (2.02 g, 20 mmol) and methanesulfonyl chloride (1.26 g, 11 mmol). The reaction solution was warmed up to room temperature and stirred for 3 hours. The resulting solution was washed with water (20 mL×2), dried with anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain the crude title compound tert-butyl 4-((methylsulfonyl)oxy)piperidin-1-carboxylate 3c (2.20 g) as a light yellow solid, which was directly used in the next step without further purification.

Workup

  1. washThe resulting solution was washed with water (20 mL×2)
  2. dry with materialdried with anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5a7b55ed59794372a8ed75bfc882a3ca
Source dataset
uspto-grants-2015_09
Patent number
US09139548B2

Reaction notes

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