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

HRID 1676158Notes

Reaction equation

HRID 1676158 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C(Cl)Cl>[CH3:22][S:23]([O:14][CH:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]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 100.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of tert-butyl-4-hydroxy-1-piperidinecarboxylate (10.28 g, 51.08 mmol, Aldrich) and Et3N (14.25 mL, 102.16 mmol, EMD) in CH2Cl2 (300 mL) at room temperature was added methanesulfonyl chloride (4.35 mL, 56.19 mmol, Aldrich) dropwise. The reaction mixture was stirred at room temperature for 4 h and washed with 0.1N HCl aqueous solution, H2O and brine. The organic layer was dried with Na2SO4 and concentrate in vacuo to yield 14.3 g of the crude product as a light orange solid.

Workup

  1. washwashed with 0.1N HCl aqueous solution, H2O and brine
  2. dry with materialThe organic layer was dried with Na2SO4
  3. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-8b8c4fadb8f442e781c176d2993a1d8c
Source dataset
uspto-grants-2011_08
Patent number
US08003796B2

Reaction notes

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