Trifluoroacetic acid → 3-methylazetidin-3-ol: trifluoroacetic acid

HRID 1631370Notes

Reaction equation

HRID 1631370 reaction equation
C([N:14]1[CH2:17][C:16]([CH3:19])([OH:18])[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1.[C:20]([OH:26])([C:22]([F:25])([F:24])[F:23])=[O:21]>CCO.[OH-].[OH-].[Pd+2]>[F:23][C:22]([F:25])([F:24])[C:20]([OH:26])=[O:21].[CH3:19][C:16]1([OH:18])[CH2:17][NH:14][CH2:15]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 102439891-Benzhydryl-3-methylazetidin-3-ol

Product 1

HCID 668475833-methylazetidin-3-ol: trifluoroacetic acid

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1-benzhydryl-3-methylazetidin-3-ol (0.46 g, 1.82 mmol) in EtOH (15 mL) was added TFA (0.14 mL, 1.82 mmol) and Pd(OH)2/C (0.127 g, 0.182 mmol). The reaction was subjected to hydrogenation (50 psi) on a Parr shaker at ambient temperature overnight. The reaction mixture was filtered, concentrated and triturated with Et2O. The fine white solid was filtered to yield the product as a TFA salt.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. customtriturated with Et2O
  4. filtrationThe fine white solid was filtered

Sources & evidence

ORD record
ord-99bc4a5e70a8453f8f10aed22a973a31
Source dataset
uspto-grants-2014_07
Patent number
US08791123B2

Reaction notes

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