ChemicalBook CAS DataBase List endo-8-Methyl-8-azabicyclo[3.2.1]octane-3-methanol

endo-8-Methyl-8-azabicyclo[3.2.1]octane-3-methanol synthesis

9synthesis methods

Product Name:endo-8-Methyl-8-azabicyclo[3.2.1]octane-3-methanol
CAS Number:142892-37-3
Molecular formula:C9H17NO
Molecular Weight:155.24

273376-39-9 Synthesis

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

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endo-8-Methyl-8-azabicyclo[3.2.1]octane-3-methanol

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Yield: 97%

Reaction Conditions:

with lithium aluminium tetrahydride in tetrahydrofuran at 80; for 1 h;Microwave irradiation;

Steps:

1.a
Example 1 : 3-((Endo)-8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-2,2-diphenyl-propionitrile, TFA salt a) Preparation of ((endo^δ-methyl-δ-aza-bicycloβ^.iloct-S-yO-methanolA mixture of 1 ,1-dimethylethyl (endo)-3-(hydroxymethyl)-8-azabicyclo[3.2.1] octane-8- carboxylate (0.50 g, 2.05 mmol) and LiAIH₄ (6.16 ml_, 1.0 M in THF, 6.16 mmol) was heated at 8O⁰C with a microwave reactor for 60 min. The solution was then mixed with saturatedNa₂SO₄ solution, ethyl ether was added, dried over potassium carbonate and filtered through celite and concentrated to afford the title compound (0.31 g, 97 %): LCMS (ES) m/z 156 (M+H)⁺; ¹H-NMR(CDCI₃) 5 1.28 (s, 1 H), 1.59 (m, 4H), 1.90 (m, 1 H), 2.13 (m, 4H), 2.32 (s, 3H), 3.17 (s, 2H), 3.59 (d, 2H)

References:

GLAXO GROUP LIMITED WO2009/36243, 2009, A1 Location in patent:Page/Page column 15-16

Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

1000210-73-0
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142892-37-3
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References

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142892-37-3
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References

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142892-37-3
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References

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142892-37-3
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References