1,1-Dimethylethyl 2-Oxa-8-azaspiro[4.5]decane-8-carboxylate

Base Information

• Chemical Name: 1,1-Dimethylethyl 2-Oxa-8-azaspiro[4.5]decane-8-carboxylate
• CAS No.: 374794-96-4
• Molecular Formula: C₁₃H₂₃NO₃
• Molecular Weight: 241.331
• Mol file: 374794-96-4.mol

Synonyms:1,1-Dimethylethyl2-Oxa-8-azaspiro[4.5]decane-8-carboxylate

Chemical Property of 1,1-Dimethylethyl 2-Oxa-8-azaspiro[4.5]decane-8-carboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 333.508°C at 760 mmHg
• PKA: -0.77±0.20(Predicted)
• Flash Point: 155.501°C
• PSA: 38.77000
• Density: 1.084g/cm³
• LogP: 2.36190
• Storage Temp.: 2-8°C

Purity/Quality:

98% ^*data from raw suppliers

tert-Butyl2-oxa-8-azaspiro[4.5]decane-8-carboxylate 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,1-Dimethylethyl 2-Oxa-8-azaspiro[4.5]decane-8-carboxylate

There total 5 articles about 1,1-Dimethylethyl 2-Oxa-8-azaspiro[4.5]decane-8-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 65.0%

1,1-dimethylethyl 4-(2-hydroxyethyl)-4-(hydroxymethyl)-1-piperidinecarboxylate (236406-38-5) → 1,1-dimethylethyl 2-oxa-8-azaspiro[4,5]decane-8-carboxylate (374794-96-4)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 20 ℃;

Reference yield:

1-tert-butyl 4-ethyl piperidine-1,4-dicarboxylate (142851-03-4) → 1,1-dimethylethyl 2-oxa-8-azaspiro[4,5]decane-8-carboxylate (374794-96-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: KHMDS / tetrahydrofuran / -78 °C

1.2: tetrahydrofuran / 1 h / -78 °C

2.1: O₃ / methanol; CH₂Cl₂ / -78 °C

2.2: NaBH₄ / 3 h / -78 - 20 °C

3.1: p-TsOH / toluene / 3 h / Heating

4.1: DIBAL-H / CH₂Cl₂ / 5 h / -78 - 0 °C

5.1: PPh₃; diethyl azodicarboxylate / tetrahydrofuran / 16 h / 0 - 20 °C

With potassium hexamethylsilazane; diisobutylaluminium hydride; toluene-4-sulfonic acid; ozone; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; toluene; 5.1: Mitsunobu reaction;

DOI:10.1016/S0960-894X(02)00250-0

Reference yield:

1,1-dimethylethyl 1-oxo-2-oxa-8-azaspiro[4,5]decane-8-carboxylate (154348-08-0) → 1,1-dimethylethyl 2-oxa-8-azaspiro[4,5]decane-8-carboxylate (374794-96-4)

Guidance literature:

Multi-step reaction with 2 steps

1: DIBAL-H / CH₂Cl₂ / 5 h / -78 - 0 °C

2: PPh₃; diethyl azodicarboxylate / tetrahydrofuran / 16 h / 0 - 20 °C

With diisobutylaluminium hydride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; 2: Mitsunobu reaction;

DOI:10.1016/S0960-894X(02)00250-0

upstream raw materials:

1,1-dimethylethyl 4-(2-hydroxyethyl)-4-(hydroxymethyl)-1-piperidinecarboxylate

1-tert-butyl 4-ethyl piperidine-1,4-dicarboxylate

1,1-dimethylethyl 1-oxo-2-oxa-8-azaspiro[4,5]decane-8-carboxylate

1-(1,1-dimethylethyl) 4-ethyl 4-(2-propenyl)-1,4-piperidinedicarboxylate

Downstream raw materials:

2-(3,5-bis-trifluoromethyl-phenyl)-N-[4-(2-oxa-8-aza-spiro[4.5]dec-8-yl)-1-phenyl-cyclohexyl]-propionamide

2-(3,5-bis-trifluoromethyl-phenyl)-N-[4-(2-oxa-8-aza-spiro[4.5]dec-8-yl)-1-phenyl-cyclohexyl]-propionamide

2-oxa-8-azaspiro[4.5]decane

Refernces

• 1、 -. "Cyclohexane derivatives and their use as therapeutic agents". Page 30. . Retrieved 2010/02/06.