ChemicalBook CAS DataBase List ((1R,4S)-2-Azabicyclo[2.2.1]hept-5-en-3-one

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

12synthesis methods

Product Name:((1R,4S)-2-Azabicyclo[2.2.1]hept-5-en-3-one
CAS Number:79200-56-9
Molecular formula:C6H7NO
Molecular Weight:109.13

(1R,4S)-4-Aminocyclopent-2-enecarboxylic acid

134003-04-6
106 suppliers
$82.00/100mg

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

79200-56-9
224 suppliers
$10.00/1g

Yield:98 % ee

Reaction Conditions:

with (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate in N,N-dimethyl-formamide at 45; for 15 h;

Steps:

1.6; 2.6; 3.6 (6) (1R, 4S) 2-azabicyclo[2.2.1]hept-5-en-3-one

Dissolve 2.5 g of (1R, 4S) 4-aminocyclopent-2-ene-1-carboxylic acid in 10 mL of N, N-dimethylformamide, and add three7.4g of pyrrolidinylphosphonium bromide hexafluorophosphate, heated at 45°C to react for 15H. After the reaction, add water to dilute and extract with ethyl acetate. Take, wash the organic phase once with saturated ammonium chloride, wash once with saturated sodium bicarbonate, then dry the organic phase and spin dry to obtain the crude product. Ethyl acetate/n-hexane system is crystallized to obtain refined products with an ee value of 98%.

References:

CN111072547,2020,A Location in patent:Paragraph 0023; 0038-0040; 0041; 0056-0058; 0059; 0074-0076