9-Benzyl-3-oxa-9-azabicyclo(3.3.1)nonan-7-one → 3-Oxa-9-azabicyclo[3.3.1]nonan-7-one

HRID 1393202Notes

Reaction equation

HRID 1393202 reaction equation
C([N:8]1[CH:13]2[CH2:14][C:15](=[O:17])[CH2:16][CH:9]1[CH2:10][O:11][CH2:12]2)C1C=CC=CC=1>CCOC(C)=O.CC(O)=O.[Pd]>[CH:9]12[NH:8][CH:13]([CH2:14][C:15](=[O:17])[CH2:16]1)[CH2:12][O:11][CH2:10]2

Participants

4

Reactant 1

HCID 156391149-Benzyl-3-oxa-9-azabicyclo(3.3.1)nonan-7-one

Product 1

HCID 552883333-Oxa-9-azabicyclo[3.3.1]nonan-7-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 22609514Ethyl acetate acetateSolvent

Procedure

To a stirring mixture of 9-benzyl-3-oxa-9-aza-bicyclo[3.3.1]nonan-7-one (1.1 g, 4.76 mmol) in EtOAc/HOAc (6 mL, 1:1, v/v) was added palladium on carbon (250 mg). The resulting mixture was stirred at room temperature under an atmosphere of hydrogen for 2 days. The suspension was filtered through Celite and the filtrate was concentrated under vacuum to give a quantitative yield of 3-oxa-9-aza-bicyclo[3.3.1]nonan-7-one as a yellow oil. This crude mixture was converted to the corresponding hydrochloric salt by the addition of HCl (3 mL, 1N aqueous HCl). The mixture was concentrated under reduced pressure and this process was repeated twice. Retention time (min)=0.231, Method [1], MS(ESI) 142.2 (M+H).

Workup

  1. filtrationThe suspension was filtered through Celite
  2. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-170c5bf807f74809b9383a612f50339d
Source dataset
uspto-grants-2008_03
Patent number
US07345056B2

Reaction notes

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