ChemicalBook CAS DataBase List 1,1-Dimethylethyl 1-oxa-8-azaspiro[4.5]decane-8-carboxylate

1,1-Dimethylethyl 1-oxa-8-azaspiro[4.5]decane-8-carboxylate synthesis

6synthesis methods

Product Name:1,1-Dimethylethyl 1-oxa-8-azaspiro[4.5]decane-8-carboxylate
CAS Number:374794-89-5
Molecular formula:C13H23NO3
Molecular Weight:241.33

1-Piperidinecarboxylic acid, 4-hydroxy-4-(3-hydroxypropyl)-, 1,1-diMethylethyl ester

374794-88-4
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1,1-Dimethylethyl 1-oxa-8-azaspiro[4.5]decane-8-carboxylate

374794-89-5
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$408.10/250mg

Yield:374794-89-5 70%

Reaction Conditions:

with triphenylphosphine;diethylazodicarboxylate in tetrahydrofuran at 0 - 20; for 25 h;

Steps:

74 Description 74 [0423] 1,1-Dimethylethyl 1-Oxa-8-azaspiro[4,5]decane-8-carboxylate

A solution of diethyl diazenedicarboxylate (3.35 mL, 21.3 mmol) in tetrahydrofuran (50 mL) was added over 15 minutes to a stirred, cooled (0° C.) solution of 1,1-dimethylethyl 4-hydroxy-4-(3-hydroxypropyl)-1-piperidinecarboxylate (Description 73, 4.6 g, 17.8 mmol) and triphenylphosphine (5.58 g, 21.3 mmol) in tetrahydrofuran (150 mL) and the mixture was stirred at 0° C. for 1 hour, then at room temperature for 24 hours. The solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography on silica gel, eluting with isohexane/EtOAc (75:25 increasing to 50:50), to give the title compound (3.18 g, 70%). m/z (ES+) 242 (M+1).

References:

US2003/236250,2003,A1 Location in patent:Page 28

79099-07-3 Synthesis