Triethylamine → Tert-butyl 4-(methylsulfonyloxymethyl)piperidine-1-carboxylate

HRID 505867Notes

Reaction equation

HRID 505867 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.C(N(CC)CC)C.[S:23](Cl)([CH3:26])(=[O:25])=[O:24]>ClCCl>[CH3:26][S:23]([O:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 2765838Tert-butyl 4-(methylsulfonyloxymethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 10.08 g (46.81 mmol) of 1,1-dimethylethyl 4-(hydroxymethyl)piperidine-1-carboxylate and 9.90 ml (70.21 mmol) of triethylamine in 100 ml of dichloromethane, cooled to approximately 0° C., is admixed dropwise under an inert atmosphere with a solution of 4 ml (51.49 mmol) of mesyl chloride in 10 ml of dichloromethane. The bath is removed and stirring is continued at ambient temperature for 30 minutes. Water is added to the reaction mixture, the aqueous phase is separated off and extracted once with dichloromethane, the combined organic phases are washed with water and dried over sodium sulphate and the filtrate is concentrated under reduced pressure.

Workup

  1. customThe bath is removed
  2. additionWater is added to the reaction mixture
  3. customthe aqueous phase is separated off
  4. extractionextracted once with dichloromethane
  5. washthe combined organic phases are washed with water
  6. dry with materialdried over sodium sulphate
  7. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-f7426a8427a1489fb89f66c88f4c03c0
Source dataset
uspto-grants-2010_08
Patent number
US07781590B2

Reaction notes

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