8-Azabicyclo[3.2.1]octane-8-carboxylic acid, 3-(methylamino)-, 1,1-dimethylethyl ester, (3-exo)- synthesis

4synthesis methods

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)-

1307254-44-9
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8-Azabicyclo[3.2.1]octane-8-carboxylic acid, 3-(methylamino)-, 1,1-dimethylethyl ester, (3-exo)-

1307254-45-0
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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 Synthesis

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tert-butyl 3-endo-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate

143557-91-9
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8-Azabicyclo[3.2.1]octane-8-carboxylic acid, 3-[(methylsulfonyl)oxy]-, 1,1-dimethylethyl ester, (3-endo)-

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References