Ethyl diazoacetate → HCID 117697744, compound

HRID 1778482Notes

Reaction equation

HRID 1778482 reaction equation
[OH:1][CH:2]1[CH2:9][CH:8]2[N:10]([C:11]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:12])[CH:4]([CH2:5][O:6][CH2:7]2)[CH2:3]1.[N+](=[CH:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[N-]>C(Cl)Cl.CCOC(C)=O.C([O-])(=O)C.[Rh+2].C([O-])(=O)C>[CH2:27]([O:26][C:24](=[O:25])[CH2:23][O:1][CH:2]1[CH2:3][CH:4]2[N:10]([C:11]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:12])[CH:8]([CH2:7][O:6][CH2:5]2)[CH2:9]1)[CH3:28]

Participants

6

Reactant 2

HCID 12192Ethyl diazoacetateHCID 117697430HCID 117697430, compound

Product 1

HCID 117697744HCID 117697744, compoundYield 55%

Reagents, catalysts & solvents 3

HCID 21674Acetic acid, rhodium(2+) saltCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of benzyl 7-hydroxy-3-oxa-9-azabicyclo[3.3.1]nonane-9-carboxylate O (200 mg, 0.72 mmol) in DCM (4 mL) was added ethyl 2-diazoacetate (202 mg, 1.44 mmol) and Rhodium(II) acetate (319 mg, 0.72 mmol) at 0° C. The resulting mixture was stirred at room temperature for overnight, and then diluted with EtOAc. The organic layer was separated, and the aqueous phase was extracted with EtOAc. The combined organic phases were washed with water and brine and dried (Na2SO4). The organic solvent was removed in vacuo to give the crude product, which was purified by column chromatography to give the intermediate benzyl 7-(2-ethoxy-2-oxo-ethoxy)-3-oxa-9-azabicyclo[3.3.1]nonane-9-carboxylate (144 mg, 55%). LC/MS: calc'd 364 (MH+), exp 364 (MH+).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous phase was extracted with EtOAc
  3. washThe combined organic phases were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. customThe organic solvent was removed in vacuo
  6. customto give the crude product, which
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-5440a09271e448c1a59d02bf77c8d90d
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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