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

HRID 16609Notes

Reaction equation

HRID 16609 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]carbamateYield 58.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-benzoyl-4-tert-butoxycarbonylaminomethyl-4-fluoropiperidine (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 a colorless solid 1.77 g (58%) as the titled 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

Sources & evidence

ORD record
ord-a4ae0e0299e042ff87863631cd2d1504
Source dataset
uspto-grants-2010_06
Patent number
US07737163B2

Reaction notes

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