(S)-5-Oxo-pyrrolidine-2-carboxylic acid [(3S,8aR)-3-(tert-butyl-dimethyl-silanyloxymethyl)-7-cyclohexyl-5-oxo-1,2,3,5,8,8a-hexahydro-indolizin-6-yl]-amide

Base Information

• Chemical Name: (S)-5-Oxo-pyrrolidine-2-carboxylic acid [(3S,8aR)-3-(tert-butyl-dimethyl-silanyloxymethyl)-7-cyclohexyl-5-oxo-1,2,3,5,8,8a-hexahydro-indolizin-6-yl]-amide
• CAS No.: 183813-75-4
• Molecular Formula: C₂₆H₄₃N₃O₄Si
• Molecular Weight: 489.731
• Mol file: 183813-75-4.mol

Synonyms:(S)-5-Oxo-pyrrolidine-2-carboxylic acid [(3S,8aR)-3-(tert-butyl-dimethyl-silanyloxymethyl)-7-cyclohexyl-5-oxo-1,2,3,5,8,8a-hexahydro-indolizin-6-yl]-amide

Chemical Property of (S)-5-Oxo-pyrrolidine-2-carboxylic acid [(3S,8aR)-3-(tert-butyl-dimethyl-silanyloxymethyl)-7-cyclohexyl-5-oxo-1,2,3,5,8,8a-hexahydro-indolizin-6-yl]-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-5-Oxo-pyrrolidine-2-carboxylic acid [(3S,8aR)-3-(tert-butyl-dimethyl-silanyloxymethyl)-7-cyclohexyl-5-oxo-1,2,3,5,8,8a-hexahydro-indolizin-6-yl]-amide

There total 8 articles about (S)-5-Oxo-pyrrolidine-2-carboxylic acid [(3S,8aR)-3-(tert-butyl-dimethyl-silanyloxymethyl)-7-cyclohexyl-5-oxo-1,2,3,5,8,8a-hexahydro-indolizin-6-yl]-amide 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:

1-((S)-2-Hydroxymethyl-pyrrolidin-1-yl)-2-(1-vinyl-cyclohexyl)-ethanone (183593-62-6) → (S)-5-Oxo-pyrrolidine-2-carboxylic acid [(3S,8aR)-3-(tert-butyl-dimethyl-silanyloxymethyl)-7-cyclohexyl-5-oxo-1,2,3,5,8,8a-hexahydro-indolizin-6-yl]-amide (183813-75-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) NaH / 1.) THF, RT, 30 min, 2.) THF, RT, overnight

2: 74 percent / tetraethylammonium tosylate / carbon rod anode, Pt cathode

3: 94 percent / TiCl₄ / CH₂Cl₂ / Ambient temperature

4: 94 percent / H₂, MeONa / 5percent Pd/C

5: 95 percent / DBU / CH₂Cl₂ / 1 h / Ambient temperature

6: 1.) LDA, 2.) O₂ / 1.) THF, -78 deg C, 45 min, 2.) THF, -78 deg C, 30 min

7: 39 percent / NH₃ / methanol / 72 h / Ambient temperature

8: 1.) HOBt, 2.) EDCI / 1.) CH₂Cl₂, 0 deg C, 5 min, 2.) CH₂Cl₂, RT, overnight

With ammonia; hydrogen; oxygen; sodium methylate; titanium tetrachloride; sodium hydride; tetraethylammonium tosylate; benzotriazol-1-ol; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1021/ja961887v

Reference yield:

(S)-7-(1-Chloro-cyclohexyl)-3-hydroxymethyl-hexahydro-indolizin-5-one → (S)-5-Oxo-pyrrolidine-2-carboxylic acid [(3S,8aR)-3-(tert-butyl-dimethyl-silanyloxymethyl)-7-cyclohexyl-5-oxo-1,2,3,5,8,8a-hexahydro-indolizin-6-yl]-amide (183813-75-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 94 percent / H₂, MeONa / 5percent Pd/C

2: 95 percent / DBU / CH₂Cl₂ / 1 h / Ambient temperature

3: 1.) LDA, 2.) O₂ / 1.) THF, -78 deg C, 45 min, 2.) THF, -78 deg C, 30 min

4: 39 percent / NH₃ / methanol / 72 h / Ambient temperature

5: 1.) HOBt, 2.) EDCI / 1.) CH₂Cl₂, 0 deg C, 5 min, 2.) CH₂Cl₂, RT, overnight

With ammonia; hydrogen; oxygen; sodium methylate; benzotriazol-1-ol; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1021/ja961887v

Reference yield:

1-((S)-2-Benzyloxymethyl-pyrrolidin-1-yl)-2-(1-vinyl-cyclohexyl)-ethanone (183593-51-3) → (S)-5-Oxo-pyrrolidine-2-carboxylic acid [(3S,8aR)-3-(tert-butyl-dimethyl-silanyloxymethyl)-7-cyclohexyl-5-oxo-1,2,3,5,8,8a-hexahydro-indolizin-6-yl]-amide (183813-75-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 74 percent / tetraethylammonium tosylate / carbon rod anode, Pt cathode

2: 94 percent / TiCl₄ / CH₂Cl₂ / Ambient temperature

3: 94 percent / H₂, MeONa / 5percent Pd/C

4: 95 percent / DBU / CH₂Cl₂ / 1 h / Ambient temperature

5: 1.) LDA, 2.) O₂ / 1.) THF, -78 deg C, 45 min, 2.) THF, -78 deg C, 30 min

6: 39 percent / NH₃ / methanol / 72 h / Ambient temperature

7: 1.) HOBt, 2.) EDCI / 1.) CH₂Cl₂, 0 deg C, 5 min, 2.) CH₂Cl₂, RT, overnight

With ammonia; hydrogen; oxygen; sodium methylate; titanium tetrachloride; tetraethylammonium tosylate; benzotriazol-1-ol; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1021/ja961887v

upstream raw materials:

(3S,8aR)-6-Amino-3-(tert-butyl-dimethyl-silanyloxymethyl)-7-cyclohexyl-2,3,8,8a-tetrahydro-1H-indolizin-5-one

L-Pyroglutamic acid

1-((S)-2-Hydroxymethyl-pyrrolidin-1-yl)-2-(1-vinyl-cyclohexyl)-ethanone

1-((S)-2-Benzyloxymethyl-pyrrolidin-1-yl)-2-(1-vinyl-cyclohexyl)-ethanone

Downstream raw materials:

(3S,8aR)-7-Cyclohexyl-5-oxo-6-[((S)-5-oxo-pyrrolidine-2-carbonyl)-amino]-1,2,3,5,8,8a-hexahydro-indolizine-3-carboxylic acid

(S)-5-Oxo-pyrrolidine-2-carboxylic acid ((3S,8aR)-7-cyclohexyl-3-hydroxymethyl-5-oxo-1,2,3,5,8,8a-hexahydro-indolizin-6-yl)-amide