(2S,5S)-2-[(dimethylphenylsilanyl)methyl]-6-vinyl-1-azaspiro[4.5]decane-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: (2S,5S)-2-[(dimethylphenylsilanyl)methyl]-6-vinyl-1-azaspiro[4.5]decane-1-carboxylic acid benzyl ester
• CAS No.: 438461-64-4
• Molecular Formula: C₂₈H₃₇NO₂Si
• Molecular Weight: 447.693
• Mol file: 438461-64-4.mol

Synonyms:(2S,5S)-2-[(dimethylphenylsilanyl)methyl]-6-vinyl-1-azaspiro[4.5]decane-1-carboxylic acid benzyl ester

Chemical Property of (2S,5S)-2-[(dimethylphenylsilanyl)methyl]-6-vinyl-1-azaspiro[4.5]decane-1-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5S)-2-[(dimethylphenylsilanyl)methyl]-6-vinyl-1-azaspiro[4.5]decane-1-carboxylic acid benzyl ester

There total 8 articles about (2S,5S)-2-[(dimethylphenylsilanyl)methyl]-6-vinyl-1-azaspiro[4.5]decane-1-carboxylic acid benzyl 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:

(S)-5-[(Dimethyl-phenyl-silanyl)-methyl]-2-hydroxy-2-((Z)-7-trimethylsilanyl-hept-5-enyl)-pyrrolidine-1-carboxylic acid benzyl ester (1026985-49-8) → (2S,5S)-2-[(dimethylphenylsilanyl)methyl]-6-vinyl-1-azaspiro[4.5]decane-1-carboxylic acid benzyl ester (438461-64-4)

Guidance literature:

With 4 A molecular sieve; boron trifluoride diacetate; In dichloromethane; at -78 - 20 ℃;

DOI:10.1021/jo0201070

Reference yield:

(S)-(-)-5-(Bromomethyl)-2-pyrrolidinone (72479-05-1) → (2S,5S)-2-[(dimethylphenylsilanyl)methyl]-6-vinyl-1-azaspiro[4.5]decane-1-carboxylic acid benzyl ester (438461-64-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 92 percent / Li; CuCN / tetrahydrofuran / 19 h / -40 - -20 °C

2.1: 96 percent / KH / tetrahydrofuran / 0.92 h / 0 - 20 °C

3.1: t-BuLi / diethyl ether; pentane / 1.67 h / -78 - 20 °C

3.2: diethyl ether; pentane / 4 h / -78 - -20 °C

4.1: 828 mg / BF₃*2HOAc; 4 Angstroem molecular sieves / CH₂Cl₂ / -78 - 20 °C

With 4 A molecular sieve; tert.-butyl lithium; boron trifluoride diacetate; lithium; potassium hydride; In tetrahydrofuran; diethyl ether; dichloromethane; pentane;

DOI:10.1021/jo0201070

Reference yield:

7-trimethylsilanylhept-5-en-1-ol (92121-08-9) → (2S,5S)-2-[(dimethylphenylsilanyl)methyl]-6-vinyl-1-azaspiro[4.5]decane-1-carboxylic acid benzyl ester (438461-64-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 85 percent / I₂; PPh₃; imidazole / CH₂Cl₂ / 1.5 h / 0 - 20 °C

2.1: t-BuLi / diethyl ether; pentane / 1.67 h / -78 - 20 °C

2.2: diethyl ether; pentane / 4 h / -78 - -20 °C

3.1: 828 mg / BF₃*2HOAc; 4 Angstroem molecular sieves / CH₂Cl₂ / -78 - 20 °C

With 1H-imidazole; 4 A molecular sieve; iodine; tert.-butyl lithium; boron trifluoride diacetate; triphenylphosphine; In diethyl ether; dichloromethane; pentane;

DOI:10.1021/jo0201070

upstream raw materials:

(S)-5-[(Dimethyl-phenyl-silanyl)-methyl]-2-hydroxy-2-((Z)-7-trimethylsilanyl-hept-5-enyl)-pyrrolidine-1-carboxylic acid benzyl ester

(S)-(-)-5-(Bromomethyl)-2-pyrrolidinone

7-trimethylsilanylhept-5-en-1-ol

benzyl chloroformate

Downstream raw materials:

2-hydroxymethyl-6-vinyl-1-azaspiro[4.5]decane-1-carboxylic acid benzyl ester

6-(3,3-dimethoxypropyl)-2-hydroxymethyl-1-azaspiro[4.5]decane-1-carboxylic acid benzyl ester