HCID 70009058, compound → HCID 70009050, compound

HRID 1267879Notes

Reaction equation

HRID 1267879 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:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:11][C@H:12]2[S:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:26])=[O:25])C1C=CC=CC=1.[H][H]>CO.C(O)(=O)C.[Pd]>[NH2:8][C@@H:9]1[CH2:15][CH2:14][C@@H:13]2[NH:16][C@@:10]1([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:11][C@H:12]2[S:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:26])=[O:25]

Participants

6

Reactant 2

HCID 70009058HCID 70009058, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70009050HCID 70009050, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

(1R*,2R*,5S*,6R*)-2-benzylamino-8-benzyl-1-phenyl-6-phenylsulphonyl-8-azabicyclo[3.2.1]octane (Description 4; 1.73 g, 3.3 mmol) was dissolved in a mixture of methanol (30 mL) and acetic acid (20 mL), then treated with 10% palladium on charcoal (500 mg). The suspension was hydrogenated at 50 psi hydrogen for 16 hours, then filtered and concentrated. The residue was basified with saturated sodium bicarbonate solution (100 mL) and extracted with dichloromethane (2×100 mL). The extracts were dried (MgSO4) and concentrated, and the residue purified by silica chromatography to give the title compound as a gum (1.10 g, 3.2 mmol).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. extractionextracted with dichloromethane (2×100 mL)
  4. dry with materialThe extracts were dried (MgSO4)
  5. concentrationconcentrated
  6. customthe residue purified by silica chromatography

Sources & evidence

ORD record
ord-8bef065b421c4465b212ddae7878ae67
Source dataset
uspto-grants-2003_04
Patent number
US06555552B2

Reaction notes

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