1-(Diphenylmethyl)azetidin-3-ol → 1-(Diphenylmethyl)azetidin-3-one

HRID 2221001Notes

Reaction equation

HRID 2221001 reaction equation
[CH:1]([N:14]1[CH2:17][CH:16]([OH:18])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)Cl>[CH:1]([N:14]1[CH2:17][C:16](=[O:18])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 3304481-(Diphenylmethyl)azetidin-3-ol

Product 1

HCID 37355581-(Diphenylmethyl)azetidin-3-oneYield 52.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-benzhydryl-azetidin-3-ol (640 mg) in methylene chloride (6.0 mL) was added 4 Å molecular sieves. The reaction vessel was purged with nitrogen followed by addition of NMO (800 mg) and then TPAP (42 mg). The reaction was stirred over night and then filtered through a plug of silica to yield 335 mg of the title compound as a clear, colorless oil. 1H NMR (CDCl3, 300 MHz) δ ppm 4.03 (s, 4H), 4.61 (s, 1H), 7.25 (m, 2H), 7.32 (m, 4H), 7.50 (m, 4H).

Workup

  1. customThe reaction vessel was purged with nitrogen
  2. additionfollowed by addition of NMO (800 mg)
  3. filtrationfiltered through a plug of silica

Sources & evidence

ORD record
ord-fa4ddf5767b041bf9e25a59ccbdd2eaa
Source dataset
uspto-grants-2008_05
Patent number
US07368453B2

Reaction notes

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