ChemicalBook CAS DataBase List 2-Boc-7-oxo-2-Azaspiro[4.4]nonane

2-Boc-7-oxo-2-Azaspiro[4.4]nonane synthesis

5synthesis methods

Product Name:2-Boc-7-oxo-2-Azaspiro[4.4]nonane
CAS Number:1319716-42-1
Molecular formula:C13H21NO3
Molecular Weight:239.31

7-Hydroxy-2-aza-spiro[4.4]nonane-2-carboxylic acid tert-butyl ester

1319716-41-0
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1319716-42-1
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$90.00/25mg

Yield: 62%

Reaction Conditions:

with Dess-Martin periodane in dichloromethane at 0 - 20;Inert atmosphere;

Steps:

15.5 Step 5) fey -butyl 7-oxo-2-azaspiro[4.4]nonane-2-carboxylate
[382] To a suspension of terf-butyl 7-hydroxy-2-azaspiro[4.4]nonane-2-carboxylate (2.10 g, 8.70 mmol) in anhydrous DCM (25 mL) was added Dess-Martin (4.43 g, 10.44 mmol) at 0 °C under nitrogen atmosphere, and then the mixture was moved to room temperature and stirred overnight. The mixture was cooled down to 0 °C and added DCM (50 mL), then added saturated NaHC03 aqueous solution (30 mL) and saturated Na2S2( aqueous solution (30 mL). The separated organic phase was washed with a mixture of saturated NaHC0₃ aqueous solution (15 mL) and saturated Na2S203 aqueous solution (15 mL) again. The combined aqueous phases were extracted with DCM (50 mLx3). The combined organic phases were washed with saturated brine (50 mL), dried over anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (PE/EtOAc (v/v) = 3/1) to give the title compound as yellow liquid (1.30 g, 62%). MS (ESI, pos. ion) m z: 184.2 [(M-C₄)+H]⁺; 'H NMR (600 MHz, CDCI₃) δ (ppm): 3.56-3.36 (m, 2H), 3.36-3.24 (m, 2H), 2.39-2.32 (m, 2H), 2.32-2.19 (m, 2H), 2.04-1.91 (m, 2H), 1.90-1.82 (m, 2H), 1.47 (s, 9H).

References:

CALITOR SCIENCES, LLC;SUNSHINE LAKE PHARMA CO., LTD.;XI, Ning;LI, Minxiong;HU, Haiyang;WANG, Tingjin WO2015/94803, 2015, A1 Location in patent:Paragraph 382

1-Pyrrolidinecarboxylic acid, 2-oxo-3,3-di-2-propen-1-yl-, 1,1-dimethylethyl ester

1319716-35-2
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1319716-42-1
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References

2-Azaspiro[4.4]non-7-ene-2-carboxylic acid, 1-oxo-, 1,1-dimethylethyl ester

1319716-36-3
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1319716-42-1
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References

85909-08-6 Synthesis

85909-08-6
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$6.00/1g

1319716-42-1
51 suppliers
$90.00/25mg

References

24424-99-5 Synthesis

24424-99-5
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$13.50/25G

1319716-42-1
51 suppliers
$90.00/25mg

References