Water → tert-Butyl [(4-fluoropiperidin-4-yl)methyl]carbamate

HRID 733107Notes

Reaction equation

HRID 733107 reaction equation
C([N:9]1[CH2:14][CH2:13][C:12]([CH2:16][NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])([F:15])[CH2:11][CH2:10]1)(=O)C1C=CC=CC=1.[OH-].[Na+].O>C(O)C>[C:21]([O:20][C:18]([NH:17][CH2:16][C:12]1([F:15])[CH2:11][CH2:10][NH:9][CH2:14][CH2:13]1)=[O:19])([CH3:24])([CH3:22])[CH3:23]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 67231354N-benzoyl-4-tert-butoxycarbonylaminomethyl-4-fluoropiperidine

Product 1

HCID 53415226tert-Butyl [(4-fluoropiperidin-4-yl)methyl]carbamate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-benzoyl-4-tert-butoxycarbonylaminomethyl-4-fluoro piperidine (step 3 of Example 15) (4.42 g, 13.1 mmol), NaOH (2.62 g, 65.5 mmol), H2O (9.00 mL) and ethanol (90.0 mL) was refluxed for 15 h and concentrated in vacuo. To the resulting residue were added water and chloroform. The organic layer was separated, dried over magnesium sulfate, and concentrated under reduced pressure. Recrystallization of the resulting solid with hexane-CH2Cl2 afforded colorless solid 1.77 g (58%) as the title compound.

Workup

  1. temperaturewas refluxed for 15 h
  2. concentrationconcentrated in vacuo
  3. additionTo the resulting residue were added water and chloroform
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customRecrystallization of the resulting solid with hexane-CH2Cl2 afforded colorless solid 1.77 g (58%) as the title compound

Sources & evidence

ORD record
ord-5ac9d39951244c88832fd4b5d225131d
Source dataset
uspto-grants-2009_09
Patent number
US07589109B2

Reaction notes

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