2,8-Diazaspiro[4.5]decane-2-carboxylic acid, 8-cyclobutyl-, 1,1-dimethylethyl ester synthesis

4synthesis methods

Product Name:2,8-Diazaspiro[4.5]decane-2-carboxylic acid, 8-cyclobutyl-, 1,1-dimethylethyl ester
CAS Number:1001054-52-9
Molecular formula:C17H30N2O2
Molecular Weight:294.4323

1191-95-3 Synthesis

1191-95-3
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tert-Butyl 2,8-diazaspiro[4.5]decane-2-carboxylate

336191-17-4
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2,8-Diazaspiro[4.5]decane-2-carboxylic acid, 8-cyclobutyl-, 1,1-dimethylethyl ester

1001054-52-9
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Yield:-

Reaction Conditions:

Stage #1: cyclobutanone;tert-butyl 2,8-diazaspiro[4.5]decane-2-carboxylatewith triethylamine in dichloromethane at 0; for 0.5 h;
Stage #2: with sodium tris(acetoxy)borohydride in dichloromethane at 20;

Steps:

2.N.3

tert-Butyl 2,8-diazaspiro[4.5]decane-2-carboxylate (7.21 g, 30.0 mmol) is dissolved in TEA (7.69 mL) in DCM (200 mL) at 0° C. and treated dropwise with cyclobutanone (2.92 mL, 38.9 mmol). The mixture is stirred for 30 min and sodium triacetoxyborohydride (9.53 g, 4.56 mmol) is added in portions. The reaction mixture is stirred at rt overnight, basified with 1N NaOH solution and extracted with DCM (2×100 mL). The combined extracts are washed with water, brine, dried over anhydrous Na₂SO₄and concentrated in vacuo to afford the title compound. LC-MS (Method 1): 295.4.

References:

US2008/247964,2008,A1 Location in patent:Page/Page column 35

24424-99-5 Synthesis

24424-99-5
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1001054-52-9
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References

336191-15-2
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References

336191-16-3 Synthesis

tert-Butyl 8-benzyl-2,8-diazaspiro[4.5]decane-2-carboxylate

336191-16-3
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References