HCID 67006272, compound → 3-[4a-(4-Chloro-benzenesulfonyl)-5,8-difluoro-2,3,4,4a,10,10a-hexahydro-9-oxa-1-aza-phenanthren-1-yl]-propan-1-ol

HRID 564338Notes

Reaction equation

HRID 564338 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][N:12]1[CH:25]2[C:16]([S:28]([C:31]3[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=3)(=[O:30])=[O:29])([C:17]3[C:22]([O:23][CH2:24]2)=[C:21]([F:26])[CH:20]=[CH:19][C:18]=3[F:27])[CH2:15][CH2:14][CH2:13]1)C1C=CC=CC=1>C(OCC)(=O)C.[OH-].[Pd+2].[OH-]>[Cl:37][C:34]1[CH:35]=[CH:36][C:31]([S:28]([C:16]23[C:17]4[C:22](=[C:21]([F:26])[CH:20]=[CH:19][C:18]=4[F:27])[O:23][CH2:24][CH:25]2[N:12]([CH2:11][CH2:10][CH2:9][OH:8])[CH2:13][CH2:14][CH2:15]3)(=[O:29])=[O:30])=[CH:32][CH:33]=1

Participants

4

Reactant 1

HCID 67006272HCID 67006272, compound

Product 1

HCID 670062093-[4a-(4-Chloro-benzenesulfonyl)-5,8-difluoro-2,3,4,4a,10,10a-hexahydro-9-oxa-1-aza-phenanthren-1-yl]-propan-1-ol

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1-(3-Benzyloxy-propyl)-4a-(4-chloro-benzenesulfonyl)-5,8-difluoro-2,3,4,4a,10,10a-hexahydro-1H-9-oxa-1-aza-phenanthrene (399.1 mg, 0.728 mmol) was dissolved in 20 ml of ethyl acetate. Palladium hydroxide (20% on carbon, 105 mg) was added and the system was purged with hydrogen gas. The reaction was stirred at room temperature for 1.5 h. More palladium hydroxide on carbon was added (203 mg) The reaction was stirred at room temperature for 3.5 h. Palladium hydroxide (307 mg) was added again and stirred for 1 h. The reaction was filter through a celite cake and concentrated. The product was purified by column using Hex./EtOAc as the eluent (gradient from 100/0 to 50/50 in 35 minutes, then to 0/100). This resulted in three products the desired product and two dechloronation products.

Workup

  1. customthe system was purged with hydrogen gas
  2. additionMore palladium hydroxide on carbon was added (203 mg) The reaction
  3. stirringwas stirred at room temperature for 3.5 h
  4. additionPalladium hydroxide (307 mg) was added again
  5. stirringstirred for 1 h
  6. filtrationThe reaction was filter through a celite cake
  7. concentrationconcentrated
  8. customThe product was purified by column
  9. wait/EtOAc as the eluent (gradient from 100/0 to 50/50 in 35 minutes

Sources & evidence

ORD record
ord-cc892cd7c84745b68fdf65bfe9348288
Source dataset
uspto-grants-2011_11
Patent number
US08067621B2

Reaction notes

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