HCID 70009058, compound → HCID 70009199, compound

HRID 1267882Notes

Reaction equation

HRID 1267882 reaction equation
C([NH:8][C@@H:9]1[CH2:15][CH2:14][C@@H:13]2[N:16]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=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[N:16]([CH2:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=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:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)(=[O:26])=[O:25]

Participants

6

Reactant 2

HCID 70009058HCID 70009058, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70009199HCID 70009199, compoundYield 48.8%

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; 8.34 g, 16 mmol) was dissolved in methanol (150 mL) and acetic acid (150 mL), then treated with 10% palladium on activated charcoal (2 g). The suspension was then hydrogenated at 50 psi hydrogen for 16 hours, then filtered. The filtrate was concentrated in vacuo, and the oil remaining suspended in saturated aqueous sodium hydrogen carbonate solution (250 mL). This was extracted with ethyl acetate (2×250 mL) and the extracts were dried (MgSO4), then concentrated. Purification by silica chromatography yielded the title compound as a gum (3.37 g, 7.8 mmol).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. extractionThis was extracted with ethyl acetate (2×250 mL)
  4. dry with materialthe extracts were dried (MgSO4)
  5. concentrationconcentrated
  6. customPurification by silica chromatography

Sources & evidence

ORD record
ord-5711a476e5064f7f8b4dc5f71a5596c9
Source dataset
uspto-grants-2003_04
Patent number
US06555552B2

Reaction notes

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