1-Benzhydryl-3-phenoxyazetidine → 3-Phenoxyazetidine

HRID 72422Notes

Reaction equation

HRID 72422 reaction equation
C([N:14]1[CH2:17][CH:16]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1>C(O)C.[Pd]>[O:18]([CH:16]1[CH2:17][NH:14][CH2:15]1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 1

HCID 28175781-Benzhydryl-3-phenoxyazetidine

Product 1

HCID 128125013-PhenoxyazetidineYield 37.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

1-benzhydryl-3-phenoxyazetidine (D20) (2.28 g, 7.23 mmol) was dissolved in ethanol (50 ml) and Pd/C (400 mg, w/w 10%) was added. The mixture was heated at 70° C. under hydrogen atmosphere (50 psi) for 18 hours then filtered off. The filtrate was concentrated to obtain a residue which was recrystallized from diethylether to provide the title compound (D48) (400 mg) as a white solid.

Workup

  1. filtrationthen filtered off
  2. concentrationThe filtrate was concentrated
  3. customto obtain a residue which
  4. customwas recrystallized from diethylether

Sources & evidence

ORD record
ord-78c2a6c5b4744b4b9a50d51856d77f05
Source dataset
uspto-grants-2014_09
Patent number
US08828987B2

Reaction notes

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