Hydrochloric Acid → 4-Amino-2-aza-2-benzyl-3-oxo-bicyclo[3,2,1]octane Hydrochloride

HRID 988372Notes

Reaction equation

HRID 988372 reaction equation
[CH2:1]([CH:8]1[C:14](=[O:15])[C:13](=[N:16]O)[CH:12]2[CH2:18][CH:9]1[CH2:10][CH2:11]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[ClH:19].[H][H]>[Pd].C(O)C>[ClH:19].[NH2:16][CH:13]1[CH:12]2[CH2:18][CH:9]([CH2:10][CH2:11]2)[CH:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[C:14]1=[O:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 865849682-Aza-2-benzyl-4-oximino-3-oxo-bicyclo[3,2,1]octaneHCID 178418361HCID 178418361, compound

Product 1

HCID 223121994-Amino-2-aza-2-benzyl-3-oxo-bicyclo[3,2,1]octane HydrochlorideYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-aza-2-benzyl-4-oximino-3-oxobicyclo[3.2.1]octane in 10 mL/mmole of ethanol and 5.8 mL/mmole of 3N HCl containing 0.5 g/mmole of 10% Pd/C was saturated with hydrogen gas to 45 psi. The mixture was shaken for 3 hours and then filtered through a layer of Celite. The filtrate was dried over sodium sulfate and concentrated under reduced pressure to afford the title compound as a solid (86% yield). This procedure is further described in E. Reimann, Arch. Pharm. 310, 102-109 (1977).

Workup

  1. filtrationfiltered through a layer of Celite
  2. dry with materialThe filtrate was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-985dd4dedf4d487a969d5cc27a8d2112
Source dataset
uspto-grants-2003_10
Patent number
US06635632B1

Reaction notes

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