Tert-butyl 3-(2-ethoxy-2-oxoethylidene)-8-azabicyclo[3.2.1]octane-8-carboxylate → Tert-butyl 3-(2-ethoxy-2-oxoethyl)-8-azabicyclo[3.2.1]octane-8-carboxylate

HRID 1191500Notes

Reaction equation

HRID 1191500 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][C:11](=[CH:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:12]2)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.O=[Pt]=O>[C:1]([O:5][C:6]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][CH:11]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:12]2)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 58968477Tert-butyl 3-(2-ethoxy-2-oxoethylidene)-8-azabicyclo[3.2.1]octane-8-carboxylate

Product 1

HCID 58968458Tert-butyl 3-(2-ethoxy-2-oxoethyl)-8-azabicyclo[3.2.1]octane-8-carboxylate

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A reaction flask was charged with 3-ethoxycarbonylmethylene-8-azabicyclo[3.2.1]octane-8-carboxylic acid t-butyl ester (0.254 g, 0.86 mmol) and PtO2 (0.028 g) in MeOH (4 mL). The reaction flask was evacuated and purged with hydrogen twice followed by stirring under a hydrogen atmosphere for 20 h. The reaction mixture was filtered through Celite, washed with MeOH, and concentrated to give the crude title compound as the major isomer (0.256 g, 100%, 1:3 α:β).

Workup

  1. customThe reaction flask was evacuated
  2. custompurged with hydrogen
  3. filtrationThe reaction mixture was filtered through Celite
  4. washwashed with MeOH
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1ae1e3d3b0bf4af3b7bff265948ba713
Source dataset
uspto-grants-2014_03
Patent number
US08680115B2

Reaction notes

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