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

HRID 1616074Notes

Reaction equation

HRID 1616074 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.[CH3:23][S:24](Cl)(=[O:26])=[O:25].O>O1CCCC1>[C:12]([O:11][C:9]([N:6]1[CH2:7][CH2:8][CH:3]([CH2:2][O:1][S:24]([CH3:23])(=[O:26])=[O:25])[CH2:4][CH2:5]1)=[O:10])([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 2765838Tert-butyl 4-(methylsulfonyloxymethyl)piperidine-1-carboxylateYield 118.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere, the tert-butyl-4-hydroxymethylpiperidine-1-carboxylate obtained in Step 1 (12.9 g, crude) was dissolved in anhydrous tetrahydrofuran (100 mL), triethylamine (17 mL, 120 mmol) was added, thereafter methanesulfonyl chloride (3.5 mL, 44 mmol) was added dropwise under ice-cooling over about 10 minutes, and stirring was further conducted under ice-cooling for 30 minutes. Water was added to the reaction liquid to quench the reaction, and the reaction liquid was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under a reduced pressure to give tert-butyl-4-{[(methylsulfonyl)oxy]methyl}piperidine-1-carboxylate (15.3 g) as a crude purified product.

Workup

  1. temperaturecooling over about 10 minutes
  2. temperaturecooling for 30 minutes
  3. customto quench
  4. customthe reaction
  5. customthe reaction liquid
  6. extractionwas extracted with ethyl acetate
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-cf50dcb00ed845c3b37a569c520f6177
Source dataset
uspto-grants-2014_07
Patent number
US08765771B2

Reaction notes

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