1H-Pyrrolizin-1-amine, hexahydro-, (1S,7aR)- synthesis

7synthesis methods

Product Name:1H-Pyrrolizin-1-amine, hexahydro-, (1S,7aR)-
CAS Number:849112-03-4
Molecular formula:C7H14N2
Molecular Weight:126.2

1-Pyrrolidinecarboxylic acid, 2-hydroxy-3-[[(phenylmethoxy)carbonyl]amino]-, 1,1-dimethylethyl ester, (3S)-

849111-99-5
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1H-Pyrrolizin-1-amine, hexahydro-, (1S,7aR)-

849112-03-4
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Yield:-

Steps:

Multi-step reaction with 6 steps
1.1: 68 percent / p-TsOH*H₂O; PPTS / CH₂Cl₂ / 30 h / 20 °C
2.1: n-BuLi; lithium naphthalenide / tetrahydrofuran; hexane / 0.5 h / -78 °C
2.2: 57 percent / tetrahydrofuran; hexane / 1 h / -78 °C
3.1: BH₃*SMe₂ / hexane / 12 h / 25 - 30 °C
3.2: 50 percent / aq. NaOH; H₂O₂ / hexane; ethanol
4.1: 90 percent / Et₃N / CH₂Cl₂ / 5 h / -40 - 0 °C
5.1: 71 percent / aq. HCl / dioxane / 12 h / 20 °C
6.1: 78 percent / H₂; aq. HCl / Pd/C / 20 °C / 760 Torr

References:

Tang, Tian;Ruan, Yuan-Ping;Ye, Jian-Liang;Huang, Pei-Qiang [Synlett,2005,# 2,art. no. U28804ST,p. 231 - 234]

Carbamic acid, [(1S,7aR)-hexahydro-1H-pyrrolizin-1-yl]-, phenylmethyl ester (9CI)

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1-Pyrrolidinecarboxylic acid, 3-[[(phenylmethoxy)carbonyl]amino]-2-(phenylthio)-, 1,1-dimethylethyl ester, (3S)-

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849112-03-4
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References

1-Pyrrolidinecarboxylic acid, 2-oxo-3-[[(phenylmethoxy)carbonyl]amino]-, 1,1-dimethylethyl ester, (3S)-

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849112-03-4
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1-Pyrrolidinecarboxylic acid, 3-[[(phenylmethoxy)carbonyl]amino]-2-(2-propen-1-yl)-, 1,1-dimethylethyl ester, (2R,3S)-

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References