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

HRID 2043760Notes

Reaction equation

HRID 2043760 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 89.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1,1-dimethylethyl 4-hydroxy-1-piperidinecarboxylate (4.02 g, 20 mmol) and triethylamine (4.4 mL) in 50 mL of dichloromethane was slowly added methanesulfonylchloride (1.7 mL, 22 mmol) at 0° C. The reaction mixture was stirred for 1 h at 0° C., washed with 1 M aqueous hydrochloric acid, dried over MgSO4 and concentrated in vacuo to give 5 g of the title compound as a white solid.

Workup

  1. customat 0° C
  2. washwashed with 1 M aqueous hydrochloric acid
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e3dc494e0cb74936b82b9f793167ef4e
Source dataset
uspto-grants-2013_11
Patent number
US08586611B2

Reaction notes

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