ChemicalBook CAS DataBase List 8-Azabicyclo[3.2.1]octane-8-carboxylic acid, 3-(hydroxymethyl)-, 1,1-dimethylethyl ester, (3-endo)-

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

4synthesis methods

Product Name:8-Azabicyclo[3.2.1]octane-8-carboxylic acid, 3-(hydroxymethyl)-, 1,1-dimethylethyl ester, (3-endo)-
CAS Number:273376-39-9
Molecular formula:C13H23NO3
Molecular Weight:241.33

8-Azabicyclo[3.2.1]octane-3-methanol, 8-(phenylmethyl)-, (3-endo)-

852460-98-1
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24424-99-5 Synthesis

24424-99-5
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8-Azabicyclo[3.2.1]octane-8-carboxylic acid, 3-(hydroxymethyl)-, 1,1-dimethylethyl ester, (3-endo)-

273376-39-9
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Yield: 81%

Reaction Conditions:

Stage #1:[(3-endo)-8-(phenylmethyl)-8-azabicyclo[3.2.1]oct-3-yl]methanol with hydrogenchloride;hydrogen;palladium hydroxide on carbon in ethanol;water at 20; under 2844.39 Torr; for 66 h;
Stage #2:di-tert-butyl dicarbonate with sodium hydroxide in 1,3-dioxane;water at 20;

Steps:

A solution of (3-endo)- (8-benzyl-8-azabicyclo [3.2. 1] oct-3-yl) methanol (2.31 g, 10 mmol) in ethanol (45 ml) and 6N HCI (2 ml) containing palladium hydroxide on carbon (Pearlman's catalyst, 2.6 g, 20% (w/w) ) was hydrogenated (55 psi H2) at room temperature for 18 h. After filtration of the catalyst, the filtrate was concentrated under vacuum. The residue was redissolved in EtOH (45 ml) and 6N HCI (2ml), to which palladium hydroxide on carbon (2.6 g) was added. The reaction mixture was hydrogenated (55 psi H2) at room temperature for 2 days. The catalyst was filtered off over Celite and the filtrate was evaporated. The residue and di-tert-butyl dicarbonate (3.2 g, 15 mmol) were dissolved in 60 ml of dioxane : 1 N NaOH (2: 1) and stirred overnight at room temperature. The solvent was evaporated and the residue partitioned between ethyl acetate (3 X 50 ml) and water (50 ml). The combined organic layers were dried over Na2SO4 and evaporated. The residual oil was purified by loading onto an aminopropyl SPE cartridge (30g) and eluting with DCM (4 X 30 ml), EA (4 X 30 ml) and MeOH (2 X 30 ml). The DCM fractions were combined and evaporated to give a colourless oil (1.95 g, 81 %). LC/MS: 1.65 min (100 %), MH+: 242. NMR (CDCI3) : 4.15 ppm (broad, 2H), 3.64 ppm (d ; 2H), 2.20 ppm (broad, 2H), 1.97 ppm (broad, 2H), 1.85 ppm (m, 1 H), 1.60 ppm (m, 2H), 1.40-1. 50 ppm (s+broad, 11 H)

References:

GLAXO GROUP LIMITED WO2005/46586, 2005, A2 Location in patent:Page/Page column 24

(1R,3r,5S)-8-Azabicyclo[3.2.1]octan-3-ylmethanol

1257512-65-4
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24424-99-5 Synthesis

24424-99-5
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$13.50/25G

273376-39-9
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$268.00/250mg

References

185099-67-6
245 suppliers
$5.00/250mg

273376-39-9
26 suppliers
$268.00/250mg

exo-8-Boc-8-azabicyclo[3.2.1]octane-3-Methanol

273207-58-2
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$179.00/250 mg

References

185099-67-6
245 suppliers
$5.00/250mg

273376-39-9
26 suppliers
$268.00/250mg

References