Cyclohexene → 3-(2-Chloroethyl)-1-(4-fluorophenyl)-4-(4-hydroxyphenyl)azetidin-2-one

HRID 2377662Notes

Reaction equation

HRID 2377662 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:11]([C:12]3[CH:17]=[CH:16][C:15]([O:18]CC4C=CC=CC=4)=[CH:14][CH:13]=3)[CH:10]([CH2:26][CH2:27][Cl:28])[C:9]2=[O:29])=[CH:4][CH:3]=1.C1CCCCC=1>CO.[OH-].[OH-].[Pd+2]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:11]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)[CH:10]([CH2:26][CH2:27][Cl:28])[C:9]2=[O:29])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 69198255HCID 69198255, compound

Product 1

HCID 691989143-(2-Chloroethyl)-1-(4-fluorophenyl)-4-(4-hydroxyphenyl)azetidin-2-oneYield 100.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

A stirring mixture of 1-(4-fluorophenyl)-3-(2-chloroethyl)-4-[4-(benzyloxy)phenyl]azetidin-2-one (prepared according to Bioorg. Med. Chem. Lett. 1996, 6, 1271-1274; 2.00 g, 4.88 mmol), Pd(OH)2/C (0.500 g, 20%) and cyclohexene (6 ml) in MeOH (60 ml) was heated to 70° C. After 2 hours, the reaction mixture was cooled to room temperature and was filtered through diatomaceous earth. The solvent was removed under reduced pressure to give the title compound (1.57 g; -quantitative yield). No further purification was necessary. NMR (CD3OD, 400 MHz) 2.20-2.40 (m, 2H), 3.20-3.40 (m, 1H), 3.70 (t, 2H), 4.85 (d, 1H), 6.75-6.80 (m, 2H), 6.90-7.00 (m, 2H), 7.15-7.30 (m, 4H); m/z: 320.0.

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. filtrationwas filtered through diatomaceous earth
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a8917fe321ce40fa95314ee7a7c6d42d
Source dataset
uspto-grants-2008_12
Patent number
US07470678B2

Reaction notes

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