(1R*,2R*,3S*,5S*,6R*)-2-Benzylamino-8-benzyl-3-fluoro-1-phenyl-6-(hydroxymethyl)-8-azabicyclo[3.2.1]octane → (1R*,2R*,3S*,5S*,6R*)-2-Amino-3-fluoro-1-phenyl-6-(hydroxymethyl)-8-azabicyclo[3.2.1]octane

HRID 1267902Notes

Reaction equation

HRID 1267902 reaction equation
C([NH:8][C@H:9]1[C@@H:15]([F:16])[CH2:14][C@@H:13]2[N:17](CC3C=CC=CC=3)[C@@:10]1([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:11][C@H:12]2[CH2:25][OH:26])C1C=CC=CC=1>C(O)C.C1CC=CCC=1.[Pd]>[NH2:8][C@H:9]1[C@@H:15]([F:16])[CH2:14][C@@H:13]2[NH:17][C@@:10]1([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:11][C@H:12]2[CH2:25][OH:26]

Participants

5

Reactant 1

HCID 70008699(1R*,2R*,3S*,5S*,6R*)-2-Benzylamino-8-benzyl-3-fluoro-1-phenyl-6-(hydroxymethyl)-8-azabicyclo[3.2.1]octane

Product 1

HCID 70007467(1R*,2R*,3S*,5S*,6R*)-2-Amino-3-fluoro-1-phenyl-6-(hydroxymethyl)-8-azabicyclo[3.2.1]octaneYield 88.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 123431,4-CyclohexadieneSolvent

Procedure

(1R*,2R*,3S*,5S*,6R*)-2-Benzylamino-8-benzyl-3-fluoro-1-phenyl-6-(hydroxymethyl)-8-azabicyclo[3.2.1]octane (Description 38; 486 mg, 1.13 mmol) was dissolved in ethanol (20 mL) and 1,4-cyclohexadiene (2 mL). 10% Palladium on activated charcoal (500 mg) was added and the suspension was heated at reflux for 24 hours. After cooling and filtration, the filtrate was concentrated in vacuo to give the title compound as a gum (257 mg, 1.0 mmol).

Workup

  1. temperaturethe suspension was heated
  2. temperatureat reflux for 24 hours
  3. temperatureAfter cooling
  4. filtrationfiltration
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-5db20b55493b43959a31af844a9f8977
Source dataset
uspto-grants-2003_04
Patent number
US06555552B2

Reaction notes

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