2,8-Diazaspiro[4.5]decane-8-carboxylic acid, 2-(4-cyanophenyl)-3-oxo-, 3-methoxy-2,2-dimethyl-3-oxopropyl ester

Base Information

• Chemical Name: 2,8-Diazaspiro[4.5]decane-8-carboxylic acid, 2-(4-cyanophenyl)-3-oxo-, 3-methoxy-2,2-dimethyl-3-oxopropyl ester
• CAS No.: 685544-63-2
• Molecular Formula: C22H27N3O5
• Molecular Weight: 413.473
• Mol file: 685544-63-2.mol

Synonyms:

Chemical Property of 2,8-Diazaspiro[4.5]decane-8-carboxylic acid, 2-(4-cyanophenyl)-3-oxo-, 3-methoxy-2,2-dimethyl-3-oxopropyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,8-Diazaspiro[4.5]decane-8-carboxylic acid, 2-(4-cyanophenyl)-3-oxo-, 3-methoxy-2,2-dimethyl-3-oxopropyl ester

There total 10 articles about 2,8-Diazaspiro[4.5]decane-8-carboxylic acid, 2-(4-cyanophenyl)-3-oxo-, 3-methoxy-2,2-dimethyl-3-oxopropyl ester 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: 84.0%

2,2-dimethyl-3-(4-nitrophenoxycarbonyloxy)propionic acid methyl ester (685544-62-1) + 4-(3-oxo-2,8-diazaspiro[4.5]decan-2-yl)benzonitrile (685544-35-8) → 2-(4-cyanophenyl)-3-oxo-2,8-diazaspiro[4.5]decane-8-carboxylic acid 2-methoxycarbonyl-2-methylpropyl ester (685544-63-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 18h;

DOI:10.1021/jm030354b

Reference yield:

8-benzyl-2-oxa-8-aza-spiro[4.5]decane-1,3-dione (34702-66-4) → 2-(4-cyanophenyl)-3-oxo-2,8-diazaspiro[4.5]decane-8-carboxylic acid 2-methoxycarbonyl-2-methylpropyl ester (685544-63-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: Et₃N / dimethylformamide / 20 °C

2.1: 3.40 g / acetic anhydride; NaOAc / 2 h / Heating

3.1: NaBH₄ / methanol / 0 - 20 °C

3.2: NaBH₄; TFA / 0 - 20 °C

3.3: 1.633 g / acetonitrile; CH₂Cl₂ / 20 °C

4.1: 89 percent / aq. NH₄OAc; Cd-Pb couple / tetrahydrofuran / 20 °C

5.1: 84 percent / DIEA / dimethylformamide / 18 h / 20 °C

With sodium tetrahydroborate; 10% Cd/Pd; ammonium acetate; sodium acetate; acetic anhydride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm030354b

Reference yield:

1-phenylmethyl-4-piperidone (3612-20-2) → 2-(4-cyanophenyl)-3-oxo-2,8-diazaspiro[4.5]decane-8-carboxylic acid 2-methoxycarbonyl-2-methylpropyl ester (685544-63-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: Et₃N; molecular sieves 4A / CH₂Cl₂ / 20 °C

2.1: 55.10 g / ethanol; H₂O / 2 h / Heating

3.1: 98 percent / aq. HCl / 72 h / Heating

4.1: DCC / dimethylformamide / 2 h / 20 °C

5.1: Et₃N / dimethylformamide / 20 °C

6.1: 3.40 g / acetic anhydride; NaOAc / 2 h / Heating

7.1: NaBH₄ / methanol / 0 - 20 °C

7.2: NaBH₄; TFA / 0 - 20 °C

7.3: 1.633 g / acetonitrile; CH₂Cl₂ / 20 °C

8.1: 89 percent / aq. NH₄OAc; Cd-Pb couple / tetrahydrofuran / 20 °C

9.1: 84 percent / DIEA / dimethylformamide / 18 h / 20 °C

With hydrogenchloride; sodium tetrahydroborate; 10% Cd/Pd; 4 A molecular sieve; ammonium acetate; sodium acetate; acetic anhydride; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 1.1: Knoevenagel condensation;

DOI:10.1021/jm030354b

upstream raw materials:

2,2-dimethyl-3-(4-nitrophenoxycarbonyloxy)propionic acid methyl ester

4-(3-oxo-2,8-diazaspiro[4.5]decan-2-yl)benzonitrile

8-benzyl-2-oxa-8-aza-spiro[4.5]decane-1,3-dione

1-phenylmethyl-4-piperidone