3-(4-(Dibenzylamino)phenyl)oxetan-3-ol → 3-(4-Aminophenyl)oxetan-3-ol

HRID 1842913Notes

Reaction equation

HRID 1842913 reaction equation
C([N:8](CC1C=CC=CC=1)[C:9]1[CH:14]=[CH:13][C:12]([C:15]2([OH:19])[CH2:18][O:17][CH2:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1>C1COCC1.CCO.[H][H].[Pd]>[NH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2([OH:19])[CH2:16][O:17][CH2:18]2)=[CH:13][CH:14]=1

Participants

6

Reactant 1

HCID 708159883-(4-(Dibenzylamino)phenyl)oxetan-3-ol

Product 1

HCID 575703463-(4-Aminophenyl)oxetan-3-olYield 127.6%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

To a stirred solution of 3-(4-(dibenzylamino)phenyl)oxetan-3-ol (1.5 g, 5.217 mmol, 1.0 eq) in THF (50 mL) and EtOH (50 mL) was added 10% Pd/C (300 mg) and the mixture was stirred in hydrogen atmosphere at 40 psi H2 for 5 h. The mixture was passed through celite, the filtrate concentrated under reduced pressure to get 3-(4-aminophenyl)oxetan-3-ol (1.1 g, 77%; TLC system: EtOAc/PE (7:3), Rf: 0.55).

Workup

  1. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-33b99637c827427f974a6ec5d87328ee
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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