m-Chloroperbenzoic acid → 3-(2,3-Difluorophenyl)-1-ethylazetidin-3-ol-1-oxide

HRID 2041889Notes

Reaction equation

HRID 2041889 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1([OH:15])[CH2:12][N:11]([CH2:13][CH3:14])[CH2:10]1.ClC1C=C(C=CC=1)C(OO)=[O:21]>ClCCl>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1([OH:15])[CH2:12][N+:11]([O-:21])([CH2:13][CH3:14])[CH2:10]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 462081043-(2,3-Difluorophenyl)-1-ethylazetidin-3-ol

Product 1

HCID 462081103-(2,3-Difluorophenyl)-1-ethylazetidin-3-ol-1-oxideYield 23.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-(2,3-difluorophenyl)-1-ethylazetidin-3-ol (0.622 g, 2.91 mmol) in dichloromethane (30 mL) was added 3-chloroperoxybenzoic acid in portions (77%, 0.98 g, 4.37 mmol). The resulting mixture was stirred at ambient temperature for 5 h. The reaction mixture was poured onto a column of basic alumina, the column was washed with dichloromethane and eluated with methanol. Purification by HPLC on waters OBD C18, 5 μm (MeOH/33 mM NH3, 10:90 to 30:70) gave the title compound (0.160 g, 23.9%). The N-oxide was converted to the hydrochloric acid salt and recrystallized from methanol/acetonitrile. The product was analyzed by LCMS (Qtrap, Applied Biosystems, Q1 MS): MS (m+1)/z; 231 (M+1, bp).

Workup

  1. additionThe reaction mixture was poured onto a column of basic alumina
  2. washthe column was washed with dichloromethane
  3. customPurification by HPLC on waters OBD C18, 5 μm (MeOH/33 mM NH3, 10:90 to 30:70)

Sources & evidence

ORD record
ord-f26768b4db9d4f62a12c56df0220bb5e
Source dataset
uspto-grants-2013_11
Patent number
US08586572B2

Reaction notes

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