3-[3-Benzyloxy-3-(4-fluoro-phenyl)-propyl]-4-(4-benzyloxy-phenyl)-1-(4-fluoro-phenyl)-azetidin-2-one → 1-(4-Fluorophenyl)-3-(3-(4-fluorophenyl)-3-hydroxypropyl)-4-(4-hydroxyphenyl)azetidin-2-one

HRID 1052899Notes

Reaction equation

HRID 1052899 reaction equation
C([O:8][CH:9]([C:38]1[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=1)[CH2:10][CH2:11][CH:12]1[CH:15]([C:16]2[CH:21]=[CH:20][C:19]([O:22]CC3C=CC=CC=3)=[CH:18][CH:17]=2)[N:14]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)[C:13]1=[O:37])C1C=CC=CC=1>CO.[Pd]>[F:36][C:33]1[CH:32]=[CH:31][C:30]([N:14]2[CH:15]([C:16]3[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=3)[CH:12]([CH2:11][CH2:10][CH:9]([C:38]3[CH:39]=[CH:40][C:41]([F:44])=[CH:42][CH:43]=3)[OH:8])[C:13]2=[O:37])=[CH:35][CH:34]=1

Participants

4

Reactant 1

HCID 667132803-[3-Benzyloxy-3-(4-fluoro-phenyl)-propyl]-4-(4-benzyloxy-phenyl)-1-(4-fluoro-phenyl)-azetidin-2-one

Product 1

HCID 49799421-(4-Fluorophenyl)-3-(3-(4-fluorophenyl)-3-hydroxypropyl)-4-(4-hydroxyphenyl)azetidin-2-oneYield 72%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10 gms of 3-[3-Benzyloxy-3-(4-fluoro-phenyl)-propyl]-4-(4-benzyloxy-phenyl)-1-(4-fluoro-phenyl)-azetidin-2-one was dissolved in 50 ml of methanol and 5 gms of 5% Pd/C was added at 20-25° C. Reaction mass was maintained about 30 minutes under hydrogen pressure. Filtered the catalyst and washed with methanol. The obtained reaction mass was distilled under vacuum at 70° C. and recrystalised from dichloromethane to produce 5 gms of 1-(4-Fluoro-phenyl)-3-[3-(4-fluoro-phenyl)-3-hydroxy-propyl]-4-(4-hydroxy-phenyl)-azetidin-2-one.

Workup

  1. customReaction mass
  2. temperaturewas maintained about 30 minutes under hydrogen pressure
  3. filtrationFiltered the catalyst
  4. washwashed with methanol
  5. customThe obtained reaction mass
  6. distillationwas distilled under vacuum at 70° C.
  7. customrecrystalised from dichloromethane

Sources & evidence

ORD record
ord-a56df7b4ab4142aba0911e4354bb02af
Source dataset
uspto-grants-2016_07
Patent number
US09388440B2

Reaction notes

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