8-Azabicyclo[3.2.1]octane-8-carboxylic acid, 3-(methylamino)-, 1,1-dimethylethyl ester, (3-exo)- synthesis
- Product Name:8-Azabicyclo[3.2.1]octane-8-carboxylic acid, 3-(methylamino)-, 1,1-dimethylethyl ester, (3-exo)-
- CAS Number:1307254-45-0
- Molecular formula:C13H24N2O2
- Molecular Weight:240.35
![8-Azabicyclo[3.2.1]octane-8-carboxylic acid, 3-[methyl[(phenylmethoxy)carbonyl]amino]-, 1,1-dimethylethyl ester, (3-exo)-](/CAS/20210305/GIF/1307254-44-9.gif)
1307254-44-9
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Yield:1307254-45-0 86%
Reaction Conditions:
with palladium on activated carbon;hydrogen in methanol at 20; for 16 h;
Steps:
3.c (c) tert-Butyl (1R,3s,5S)-3-(methylamino)-8-azabicyclo[3.2.1]octane-8-carboxylate
To a 100 mL flask was added palladium, 10% wt. on carbon (0.577 g, 0.542 mmol).
The material was exposed to nitrogen and then a solution of the product of the previous step (1.015 g, 2.71 mmol) in MeOH (54.2 mL) was slowly added by pipette.
A hydrogen gas balloon was attached.
The flask was evacuated and back-filled with hydrogen three times before opening the atmosphere fully to H2 gas.
The reaction mixture was stirred at RT for 16 h, filtered through a pad of Celite, and concentrated to afford a clear oil, which was purified by column chromatography 40 g column; 0-100% MeOH in DCM) to afford the product as a clear oil.
The column was flushed with 10:1 MeOH:TEA.
The filtrate was concentrated to provide a thick, clear oil with white solid which was dissolved in EtOAc, filtered, combined with the clear oil product and concentrated to provide the title intermediate (0.559 g, 86% yield) (m/z): [M+H]+ calcd for C13H24N2O2 241.18 found 241.3.
References:
US2017/312280,2017,A1 Location in patent:Paragraph 0276; 0279
744183-20-8
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![tert-butyl 3-endo-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate](/CAS/GIF/143557-91-9.gif)
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![8-Azabicyclo[3.2.1]octane-8-carboxylic acid, 3-[(methylsulfonyl)oxy]-, 1,1-dimethylethyl ester, (3-endo)-](/CAS/20210305/GIF/939960-39-1.gif)
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