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CYTISINE synthesis
- Product Name:CYTISINE
- CAS Number:485-35-8
- Molecular formula:C11H14N2O
- Molecular Weight:190.24
![1-Piperidinecarboxylic acid, 3-[(acetyloxy)methyl]-5-formyl-, phenylmethyl ester, (3S,5R)-](/CAS/20210305/GIF/206554-22-5.gif)
206554-22-5
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485-35-8
401 suppliers
$5.00/50mg
Yield:-
Steps:
Multi-step reaction with 11 steps
1.1: (-)-B-methoxydiisopinocampheylborane / diethyl ether / 1.25 h / -78 - 20 °C
1.2: diethyl ether / -78 - 20 °C / Acid hydrolysis
1.3: 76 percent / aq. NaOH; aq. H2O2 / 3 h / Heating
2.1: 99 percent / Et3N; DMAP / CH2Cl2 / 1.5 h / 20 °C
3.1: 87 percent / NaN3 / dimethylformamide / 2 h / 80 °C
4.1: Ph3P / tetrahydrofuran
4.2: 66 percent / H2O
5.1: 89 percent / Et3N; DMAP / CH2Cl2 / 4.5 h / 0 - 20 °C
6.1: 79 percent / Cl2Ru(CHPh)(PCy3)2 / CH2Cl2 / 12 h / Heating
7.1: 98 percent / NaOH / tetrahydrofuran / 2 h / 20 °C
8.1: 67 percent / Et3N; DMAP / CH2Cl2 / 1.5 h / 20 °C
9.1: 89 percent / NaH / tetrahydrofuran / 0 - 20 °C
10.1: 50 percent / DDQ / dioxane / 4 h / 110 °C
11.1: 78 percent / HCl / tetrahydrofuran / 3 h / Heating
References:
Danieli, Bruno;Lesma, Giordano;Passarella, Daniele;Sacchetti, Alessandro;Silvani, Alessandra;Virdis, Andrea [Organic Letters,2004,vol. 6,# 4,p. 493 - 496]
![1-Piperidinecarboxylic acid, 3-[(acetyloxy)methyl]-5-[(2R)-1,2,3,6-tetrahydro-6-oxo-2-pyridinyl]-, phenylmethyl ester, (3S,5R)-](/CAS/20210305/GIF/667940-07-0.gif)
667940-07-0
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
485-35-8
401 suppliers
$5.00/50mg