ChemicalBook CAS DataBase List 2-Azabicyclo[2.2.1]heptane-3-carboxylicacid,ethylester,(1R,3S,4S)-(9CI)

2-Azabicyclo[2.2.1]heptane-3-carboxylicacid,ethylester,(1R,3S,4S)-(9CI) synthesis

4synthesis methods

Product Name:2-Azabicyclo[2.2.1]heptane-3-carboxylicacid,ethylester,(1R,3S,4S)-(9CI)
CAS Number:214910-41-5
Molecular formula:C9H15NO2
Molecular Weight:169.22

134984-63-7 Synthesis

2-Azabicyclo[2.2.1]hept-5-ene-3-carboxylic acid, 2-[(1R)-1-phenylethyl]-, ethyl ester, (1S,3S,4R)-

134984-63-7
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2-Azabicyclo[2.2.1]heptane-3-carboxylicacid,ethylester,(1R,3S,4S)-(9CI)

214910-41-5
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Yield:214910-41-5 100%

Reaction Conditions:

with hydrogen;palladium 10% on activated carbon in ethanol;ethyl acetate; under 2585.81 Torr; for 23 h;

Steps:

6.B

A mixture of exo-Int-6c (15.8 g, 0.582 mol) and 10% Pd/C (4.07 g, 50% wet) in a 1 :2 mixture of EtOH/EtOAc (150 mL) was shaken for 23 hours in a Parr hydrogenation apparatus under an atmosphere of H₂ (50 psi). The reaction mixture was then filtered through Celite and the filtrate was concentrated in vacuo. 1H NMR analysis of the residue (10.8 g) showed some aromatic resonances present. Repetition of the hydrogenation procedure using 10%) Pd/C (2.0 g) afforded Int-6d (10.0 g, quant.) as a brown oil, which was used without further purification. 1H NMR (300 MHz, CDC1₃) δ 4.18 (q, 7= 7.2 Hz, 3H), 3.54 (s, 1H), 3.32 (s, 1H), 2.62 (s, 1H), 2.23 (s, 1H), 1.64-1.39 (m, 5H), 1.31-1.20 (m, 4H).

References:

WO2012/40923,2012,A1 Location in patent:Page/Page column 78 WO2012/50848,2012,A1 Location in patent:Page/Page column 78

ethyl (1R,3S,4S)-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.1]heptane-3-carboxylate

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References

2-Azabicyclo[2.2.1]hept-5-ene-3-carboxylicacid,ethylester,(1S,3S,4R)-(9CI)

764622-98-2
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214910-41-5
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References

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214910-41-5
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References