ChemicalBook CAS DataBase List 2-Azabicyclo[2.2.1]heptan-3-one

2-Azabicyclo[2.2.1]heptan-3-one synthesis

2synthesis methods

Product Name:2-Azabicyclo[2.2.1]heptan-3-one
CAS Number:24647-29-8
Molecular formula:C6H9NO
Molecular Weight:111.14

(1S,4R)-2-Aza-bicyclo[2.2.1]hept-5-en-3-one

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Yield:24647-29-8 100%

Reaction Conditions:

with hydrogen;palladium 10% on activated carbon in ethyl acetate at 20; for 24 h;

Steps:

23.A.A INTERMEDIATE 23; Procedure A:; Step A

A mixture of (LS)-(+)-2-AZABICYCLO [2.2. 1] hept-5-en-3-one (10.3 g, 94.4 mmol) in ethyl acetate (200 ML) and 10% Pd/C (0.5 g), was hydrogenated at room temperature. After 24 h the reaction mixture was filtered and evaporated leaving behind 10.4 g (100%) of the product that was taken in 250 mL methanol and HCI (12 M, 6 mL). The resultant mixture was stirred at room temperature, until the reaction was complete (72 h). Evaporation of methanol followed by drying under high vacuum, yielded title compound as an off white solid (16.0 g, 96%). H NMR (500 MHz, D20) : 8 3.70 (s, 3H), 3.01 (M, 1H), 2.38 (M, 1H), 2.16-1. 73 (M, 6H).

References:

WO2004/94371,2004,A2 Location in patent:Page 86

49805-30-3 Synthesis

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References