1-(2-Fluoro-4-nitrophenyl)azetidin-3-ol → 1-(4-Amino-2-fluorophenyl)azetidin-3-ol

HRID 1842994Notes

Reaction equation

HRID 1842994 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:14][CH:13]([OH:15])[CH2:12]1>C(O)C.[Pd]>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([N:11]2[CH2:12][CH:13]([OH:15])[CH2:14]2)=[C:2]([F:1])[CH:7]=1

Participants

4

Reactant 1

HCID 535516781-(2-Fluoro-4-nitrophenyl)azetidin-3-ol

Product 1

HCID 866721701-(4-Amino-2-fluorophenyl)azetidin-3-olYield 80.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of 1-(2-fluoro-4-nitrophenyl)azetidin-3-ol (160 mg, 0.75 mmol, 1.0 eq) in ethanol (10 mL) was added 10% Pd—C (20 mg) and stirred under H2 gas balloon at RT for 5 h. The reaction mixture was passed through celite and concentrated to obtain 1-(4-amino-2-fluorophenyl)azetidin-3-ol (110 mg, 80.0%, viscous oil) (TLC: EtOAc/PE (1:1), Rf: 0.1).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-7a5e88cbf7c8406ba9e0a645a65908c7
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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