Ethyl Acetate → (E)-tert-butyl 4-hydroxy-4-(4,4,4-trifluorobut-1-enyl)piperidine-1-carboxylate

HRID 2202403Notes

Reaction equation

HRID 2202403 reaction equation
C([O:4][C:5]1(/[CH:18]=[CH:19]/[CH2:20][C:21]([F:24])([F:23])[F:22])[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)(=O)C.[OH-].[Na+].CC(=O)OCC>CO>[OH:4][C:5]1(/[CH:18]=[CH:19]/[CH2:20][C:21]([F:24])([F:22])[F:23])[CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:15])[CH3:16])=[O:12])[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 90447582HCID 90447582, compound

Product 1

HCID 90447581(E)-tert-butyl 4-hydroxy-4-(4,4,4-trifluorobut-1-enyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of (E)-tert-butyl 4-acetoxy-4-(4,4,4-trifluorobut-1-enyl)piperidine-1-carboxylate (200 mg, 0.57 mmol) in methanol (5 mL) was added 2M NaOH (2 mL, 4 mmol), the mixture was held stirring at r.t. for 16 hrs, when TLC (20% EA/PE) indicated completion of the reaction. The mixture was concentrated in vacuo, the residue was diluted with brine and extracted with EtOAc, and the organic layer was concentrated in vacuo to get the crude product, which was used directly for the next step.

Workup

  1. customcompletion of the reaction
  2. concentrationThe mixture was concentrated in vacuo
  3. additionthe residue was diluted with brine
  4. extractionextracted with EtOAc
  5. concentrationthe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-e555021e296348798fe2bb6e8106c021
Source dataset
uspto-grants-2016_06
Patent number
US09365545B2

Reaction notes

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