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

HRID 1404592Notes

Reaction equation

HRID 1404592 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.[CH3:15][S:16](Cl)(=[O:18])=[O:17].C(N(CC)CC)C.O>ClCCl>[CH3:15][S:16]([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:18])=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-hydroxypiperidine-1-carboxylate (60.0 g, 0.3 mol, 1.0 eq), methanesulfonyl chloride (37.6 g, 0.33 mol, 1.1 eq), and triethylamine (36.2 g, 0.36 mol, 1.2 eq) in 600 ml of dichloromethane (DCM) was stirred at room temperature overnight. Water (300 ml) was added and the layers were separated. The aqueous layer was extracted with DCM once. The combined organics were washed with brine, dried, and evaporated to a yellowish solid, 80.5 g, in 97% yield.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with DCM once
  3. washThe combined organics were washed with brine
  4. customdried
  5. customevaporated to a yellowish solid, 80.5 g, in 97% yield

Sources & evidence

ORD record
ord-64d6af809f9b4e72b7072c8854cb52cf
Source dataset
uspto-grants-2014_12
Patent number
US08912330B2

Reaction notes

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