6-Azaspiro[2.5]octane-1-carboxylic acid ethyl ester synthesis

3synthesis methods

Product Name:6-Azaspiro[2.5]octane-1-carboxylic acid ethyl ester
CAS Number:1088498-24-1
Molecular formula:C10H17NO2
Molecular Weight:183.25

6-(Benzyloxycarbonyl)-6-azaspiro[2.5]octane-1-carboxylic acid

147610-85-3
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6-Azaspiro[2.5]octane-1-carboxylic acid ethyl ester

1088498-24-1
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Yield:1088498-24-1 44%

Reaction Conditions:

with hydrogen;5%-palladium/activated carbon in ethanol at 18 - 25;

Steps:

8.A

Example 8(4-Cyclobutylpiperazin-l-yl)(6-(tetrahydro-2H-pyran-4-yl)-6-azaspiro[2.5]octan-l- yl)methanone 102756-1 US/NS568A. Ethyl 6-azaspiror2.51octane-l-carboxylateTo semi-pure 1C (6.45 g, 20.32 mmol) in EtOH (100 mL) was added 5% Pd/C (0.649 g, 0.30 mmol) and a balloon filled with hydrogen placed on top of the reaction. The reaction was left to stir at RT over night. The mixture was filtered through Celite and the solvent removed under reduced pressure. The resulting oil was placed under high vacuum. The crude material was chromatographed on lOOg silica eluting first with 5% (7N NH₃/MeOH)/DCM then 10% 7N NH₃/MeOH)/DCM. The combined fractions were removed of solvent under reduced pressure to give 1.83g 8A as an amber oil (44%). m/z (ES+) M+l=184; HPLC fo=0.37 min; ¹H NMR (300.132 MHz, CDC13) δ 0.87 (dd, J=8.0, 4.4 Hz, IH), 1.13 (t, J=4.9 Hz, IH), 1.27 (t, J=7.1 Hz, 3H), 1.41 (q, J=5.2 Hz, 2H), 1.48-1.52 (m, 2H), 1.66-1.71 (m, 2H), 2.70-2.78 (m, IH), 2.81-2.85 (m, IH), 2.89 (t, J=5.4 Hz, 2H), 4.14 (q, J=7.1 Hz, 2H).

References:

WO2008/147314,2008,A1 Location in patent:Page/Page column 55; 56

147610-84-2 Synthesis

6-benzyl 1-ethyl 6-azaspiro[2.5]octane-1,6-dicarboxylate

147610-84-2
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1088498-24-1
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References

138163-12-9 Synthesis

138163-12-9
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References