Ammonium Acetate → Ethyl 2-(7-amino-9-benzyl-3-oxa-9-azabicyclo[3.3.1]nonan-7-yl)acetate

HRID 1778552Notes

Reaction equation

HRID 1778552 reaction equation
[CH2:1]([N:8]1[CH:13]2[CH2:14][C:15](=O)[CH2:16][CH:9]1[CH2:10][O:11][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC(=O)[CH2:21][C:22](O)=O.[C:26]([O-:29])(=[O:28])[CH3:27].[NH4+:30]>C(O)C>[NH2:30][C:15]1([CH2:27][C:26]([O:29][CH2:21][CH3:22])=[O:28])[CH2:16][CH:9]2[N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:13]([CH2:12][O:11][CH2:10]2)[CH2:14]1

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5383663-Methoxy-3-oxopropanoic acidHCID 156391149-Benzyl-3-oxa-9-azabicyclo(3.3.1)nonan-7-one

Product 1

HCID 117698022Ethyl 2-(7-amino-9-benzyl-3-oxa-9-azabicyclo[3.3.1]nonan-7-yl)acetateYield 5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 9-benzyl-3-oxa-9-azabicyclo[3.3.1]nonan-7-one (0.5 g, 2.2 mmol), 3-methoxy-3-oxo-propanoic acid (0.44 g, 3.3 mmol), ammonium acetate (0.33 g, 4.4 mmol) in ethanol (5 mL) was refluxed for 3 hours. After removal of solvent, the residue was purified by flash silica gel chromatography to afford ethyl 2-(7-amino-9-benzyl-3-oxa-9-azabicyclo[3.3.1]nonan-7-yl)acetate 146c. Yield: 5%. MS: calc'd (MH+) 319, measured (MH+) 319.

Workup

  1. temperaturewas refluxed for 3 hours
  2. customAfter removal of solvent
  3. customthe residue was purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-850567340f95408ebbf4d614c33d48cf
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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