ethyl (3S,4R)-4-amino-3-methoxypiperidine-1-carboxylate synthesis
- Product Name:ethyl (3S,4R)-4-amino-3-methoxypiperidine-1-carboxylate
- CAS Number:907572-18-3
- Molecular formula:C9H18N2O3
- Molecular Weight:202.25
29976-53-2
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Yield:-
Steps:
Multi-step reaction with 8 steps
1.1: potassium hydroxide / 0.5 h / 0 °C / Inert atmosphere
1.2: 1.5 h / 0 °C / Inert atmosphere
2.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere
2.2: 20 °C
3.1: sulfuric acid / water; tetrahydrofuran / 2 h / 60 °C
4.1: sodium tris(acetoxy)borohydride / tetrahydrofuran / 0.5 h / 0 - 20 °C
5.1: palladium 10% on activated carbon; ammonium formate / methanol / 20 - 70 °C / Inert atmosphere
6.1: sodium hydrogencarbonate / water / 14 h / 20 °C
7.1: Chiralcel OJ column / Resolution of racemate
8.1: hydrogen; palladium 10% on activated carbon; ammonium formate; hydrogenchloride / methanol / Inert atmosphere; Reflux
References:
Basarab, Gregory S.;Hill, Pamela J.;Garner, C. Edwin;Hull, Ken;Green, Oluyinka;Sherer, Brian A.;Dangel, P. Brian;Manchester, John I.;Bist, Shanta;Hauck, Sheila;Zhou, Fei;Uria-Nickelsen, Maria;Illingworth, Ruth;Alm, Richard;Rooney, Mike;Eakin, Ann E. [Journal of Medicinal Chemistry,2014,vol. 57,# 14,p. 6060 - 6082]
![1-Piperidinecarboxylic acid, 3-methoxy-4-[[(phenylmethoxy)carbonyl]amino]-, ethyl ester, (3S,4R)-](/CAS/20210305/GIF/907543-86-6.gif)
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