1-Benzhydryl-3-(4-fluorophenoxy)azetidine → 3-(4-Fluorophenoxy)azetidine

HRID 1916250Notes

Reaction equation

HRID 1916250 reaction equation
C1(C(C2C=CC=CC=2)[N:8]2[CH2:11][CH:10]([O:12][C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[CH2:9]2)C=CC=CC=1>C(O)C.[OH-].[Pd+2].[OH-]>[F:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][CH:10]2[CH2:9][NH:8][CH2:11]2)=[CH:14][CH:15]=1

Participants

4

Reactant 1

HCID 150533691-Benzhydryl-3-(4-fluorophenoxy)azetidine

Product 1

HCID 214287303-(4-Fluorophenoxy)azetidine

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Palladium hydroxide (500 mg) and 1-(diphenylmethyl)-3-(4-fluorophenoxy)azetidine (500 mg, 1.50 mmol) were combined in ethanol (50 mL) and hydrogenated at 50 psi for 18 h. The reaction mixture was then filtered through Celite and concentrated in vacuo. The residue was purified via silica gel chromatography (Eluant: 00:5:2 chloroform:MeOH: concentrated aqueous ammonium hydroxide) to provide C40. Yield: 188 mg, 1.12 mmol, 75%. LCMS m/z 168.1 (M+1). 1H NMR (400 MHz, CDCl3) δ 2.44 (br s, 1H), 3.76 (m, 2H), 3.89 (m, 2H), 4.91 (m, 1H), 6.66 (m, 2H), 6.93 (m, 2H). 13C NMR (100 MHz, CDCl3) δ 4.55, 70.81, 115.43, 115.51, 115.76, 115.99, 152.96, 156.15, 158.53.

Workup

  1. filtrationThe reaction mixture was then filtered through Celite
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified via silica gel chromatography (Eluant: 00:5:2 chloroform:MeOH: concentrated aqueous ammonium hydroxide)
  4. customto provide C40

Sources & evidence

ORD record
ord-43aceb4c6a574728a2df44ca716593d8
Source dataset
uspto-grants-2013_12
Patent number
US08618117B2

Reaction notes

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