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 522259Notes

Reaction equation

HRID 522259 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH:5]=[C:6]1[CH2:12][CH:11]2[N:13]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:8]([CH2:9][CH2:10]2)[CH2:7]1)[CH3:2].[H][H]>[Pd].CCO>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH:6]1[CH2:12][CH:11]2[N:13]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:8]([CH2:9][CH2:10]2)[CH2:7]1)[CH3:2]

Participants

5

Reactant 2

HCID 58968477Tert-butyl 3-(2-ethoxy-2-oxoethylidene)-8-azabicyclo[3.2.1]octane-8-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 58968458Tert-butyl 3-(2-ethoxy-2-oxoethyl)-8-azabicyclo[3.2.1]octane-8-carboxylateYield 99.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% palladium on carbon (about 50% wet) (170 mg) was added to a mixture of tert-butyl 3-(2-ethoxy-2-oxoethylidene)-8-azabicyclo[3.2.1]octane-8-carboxylate (1.7 g) and EtOH (34 mL), and the mixture was stirred at room temperature for 4 hours in a hydrogen atmosphere at 3 atm. The reaction mixture was separated by filtration using Celite, and the filtrate was concentrated under reduced pressure, whereby tert-butyl 3-(2-ethoxy-2-oxoethyl)-8-azabicyclo[3.2.1]octane-8-carboxylate (1.7 g) was obtained as a colorless oil.

Workup

  1. customThe reaction mixture was separated by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3f58f14ae75646bf8de39672d4453fe1
Source dataset
uspto-grants-2016_05
Patent number
US09328118B2

Reaction notes

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