HCID 70007537, compound → (1R*,2R*,5S*,6R*)-2-Amino-6-(tert-butoxycarbonyl)-1-phenyl-8-azabicyclo[3.2.1]octane

HRID 1267896Notes

Reaction equation

HRID 1267896 reaction equation
C([NH:8][C@@H:9]1[CH2:15][CH2:14][C@@H:13]2[N:16](CC3C=CC=CC=3)[C@@:10]1([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:11][C@H:12]2[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])C1C=CC=CC=1.[H][H]>[Pd].CO.C(O)(=O)C>[NH2:8][C@@H:9]1[CH2:15][CH2:14][C@@H:13]2[NH:16][C@@:10]1([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[CH2:11][C@H:12]2[C:24]([O:26][C:27]([CH3:29])([CH3:30])[CH3:28])=[O:25]

Participants

6

Reactant 2

HCID 70007537HCID 70007537, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70009467(1R*,2R*,5S*,6R*)-2-Amino-6-(tert-butoxycarbonyl)-1-phenyl-8-azabicyclo[3.2.1]octaneYield 99.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

(1R*,2R*,5S*,6R*)-2-Benzylamino-8-benzyl-6-(tert-butoxycarbonyl)-1-phenyl-8-azabicyclo[3.2.1]octane (Description 18; 7.07 g, 14.7 mmol) and 10% palladium on activated charcoal (2 g) were taken up in methanol (100 mL) and acetic acid (100 mL), and the mixture was hydrogenated at 50 psi hydrogen for 16 hours at room temperature. The suspension was filtered and the filtrate concentrated in vacuo. The residue was then suspended in saturated aqueous sodium hydrogen carbonate solution (200 mL) and extracted with dichloromethane (2×400 mL). The extracts were dried (MgSO4) and concentrated to give the title compound as a brown oil (4.4 g, 14.6 mmol).

Workup

  1. filtrationThe suspension was filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. extractionextracted with dichloromethane (2×400 mL)
  4. dry with materialThe extracts were dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-abf1ac97c7d74d82bd754a20cb78e888
Source dataset
uspto-grants-2003_04
Patent number
US06555552B2

Reaction notes

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