ChemicalBook CAS DataBase List 2-Azabicyclo[2.2.1]heptane-2-carboxylic acid, 3-oxo-, 1,1-dimethylethyl ester, (1S)-

2-Azabicyclo[2.2.1]heptane-2-carboxylic acid, 3-oxo-, 1,1-dimethylethyl ester, (1S)- synthesis

7synthesis methods

Product Name:2-Azabicyclo[2.2.1]heptane-2-carboxylic acid, 3-oxo-, 1,1-dimethylethyl ester, (1S)-
CAS Number:204913-00-8
Molecular formula:C11H17NO3
Molecular Weight:211.26

24424-99-5 Synthesis

24424-99-5
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(1S,4R)-2-Aza-bicyclo[2.2.1]hept-5-en-3-one

130931-83-8
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$8.00/100mg

2-Azabicyclo[2.2.1]heptane-2-carboxylic acid, 3-oxo-, 1,1-dimethylethyl ester, (1S)-

204913-00-8
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Yield:204913-00-8 86%

Reaction Conditions:

Stage #1: (1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-onewith hydrogen;palladium 10% on activated carbon in methanol; under 2585.81 Torr; for 1 h;
Stage #2: di-tert-butyl dicarbonatewith dmap in dichloromethane at 20;

Steps:

61.A

50 g (0.46 mol) of (1S,4R)-(+)-2-azabicyclo[2.2.1]hept-5-en-3-one in 200 mL of methanol containing 2.5 g of Pd/C (10%) was hydrogenated on a Parr Apparatus under 50 psi of hydrogen for 1 h. The catalyst was removed by filtration through a pad of celite. The filtrates were evaporated and the residue was dried in vacuum. The resulting white solid (50 g) was dissolved in 200 mL of methylene chloride and 110 g (0.50 mol) of di-tert-butyl dicarbonate and 1.0 g of DMAP were added. The reaction mixture was stirred at room temperature overnight and then loaded on a silica gel column, eluted with 10% EtOAc/Hexane. The title compound (83 g, 86%) was obtained as a white solid. ¹NMR (400 MHz, CDCl₃): 1.40 (d, 1H), 1.51 (s,9H), 1.70-1.95 (m, 5H), 2.84 (m, 1H), 4.50 (m, 1H).

References:

US2007/117797,2007,A1 Location in patent:Page/Page column 33

24424-99-5 Synthesis

24424-99-5
826 suppliers
$13.50/25G