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

HRID 2079657Notes

Reaction equation

HRID 2079657 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]>C(Cl)Cl>[C:11]([O:10][C:8]([N:5]1[CH2:4][CH2:3][CH:2]([O:1][S:23]([CH3:22])(=[O:25])=[O:24])[CH2:7][CH2:6]1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

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

Product 1

HCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl 4-hydroxypiperidine-1-carboxylate (1 eq) in methylene chloride and triethyl amine (1.4 eq) at 0° C. was added methane sulfonyl chloride (1.4 eq) drop-wise. The reaction was brought to ambient temperature and was stirred for 1 h. The reaction mixture was washed with water and saturated sodium chloride solution. The organic layer was then dried with sodium sulfate and concentrated to yield tert-butyl-4-(methylsulfonyloxy)piperidine-1-carboxylate in quantitative yield. The product was confirmed by 1H NMR, and used without further purification.

Workup

  1. customwas brought to ambient temperature
  2. washThe reaction mixture was washed with water and saturated sodium chloride solution
  3. dry with materialThe organic layer was then dried with sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0261cb0981124ee48b37da971e2a25f0
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

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