HCID 57656394, compound → HCID 57656121, compound

HRID 2041126Notes

Reaction equation

HRID 2041126 reaction equation
[CH2:1]([C:4]1[CH:20]=[CH:19][C:7]2[CH2:8][CH2:9][N:10]([C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])[CH2:11][CH2:12][C:6]=2[C:5]=1[OH:21])[CH:2]=[CH2:3]>CCOC(C)=O.[Pd]>[OH:21][C:5]1[C:6]2[CH2:12][CH2:11][N:10]([C:13](=[O:18])[C:14]([F:17])([F:15])[F:16])[CH2:9][CH2:8][C:7]=2[CH:19]=[CH:20][C:4]=1[CH2:1][CH2:2][CH3:3]

Participants

4

Reactant 1

HCID 57656394HCID 57656394, compound

Product 1

HCID 57656121HCID 57656121, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 7-allyl-6-hydroxy-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (1.5 g, 5 mmol) in EtOAc (50 mL) containing 10% Pd/C (1.3 g). Stir at ambient temperature at 1 atm with H2 (balloon) for 30 min. Filter the catalyst and wash with water (100 mL). Extract the resulting filtrate three times with EtOAc, wash the combined organic extracts with brine, dry over MgSO4, filter and concentrate in vacuo to give the desired intermediate as a white solid (1.45 g, 97%). MS (ES+) m/z: 302 (M+H)+.

Workup

  1. filtrationFilter the catalyst
  2. washwash with water (100 mL)
  3. extractionExtract the resulting filtrate three times with EtOAc
  4. washwash the combined organic extracts with brine
  5. dry with materialdry over MgSO4
  6. filtrationfilter
  7. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-90c2a37703d84c7ca095a6bb5fd5ced7
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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