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

Base Information

• Chemical Name: (3S,8aS)-7-Cyclohexyl-5-oxo-6-[((S)-5-oxo-pyrrolidine-2-carbonyl)-amino]-1,2,3,5,8,8a-hexahydro-indolizine-3-carboxylic acid
• CAS No.: 183593-59-1
• Molecular Formula: C₂₀H₂₇N₃O₅
• Molecular Weight: 389.451
• Mol file: 183593-59-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about (3S,8aS)-7-Cyclohexyl-5-oxo-6-[((S)-5-oxo-pyrrolidine-2-carbonyl)-amino]-1,2,3,5,8,8a-hexahydro-indolizine-3-carboxylic acid 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: 63.0%

(S)-5-Oxo-pyrrolidine-2-carboxylic acid ((3S,8aS)-7-cyclohexyl-3-hydroxymethyl-5-oxo-1,2,3,5,8,8a-hexahydro-indolizin-6-yl)-amide (183593-56-8) → (3S,8aS)-7-Cyclohexyl-5-oxo-6-[((S)-5-oxo-pyrrolidine-2-carbonyl)-amino]-1,2,3,5,8,8a-hexahydro-indolizine-3-carboxylic acid (183593-59-1)

Guidance literature:

With jones reagent; In acetone; at 0 - 20 ℃; for 2h;

DOI:10.1021/ja961887v

Reference yield:

1-((S)-2-Hydroxymethyl-pyrrolidin-1-yl)-2-(1-vinyl-cyclohexyl)-ethanone (183593-62-6) → (3S,8aS)-7-Cyclohexyl-5-oxo-6-[((S)-5-oxo-pyrrolidine-2-carbonyl)-amino]-1,2,3,5,8,8a-hexahydro-indolizine-3-carboxylic acid (183593-59-1)

Guidance literature:

Multi-step reaction with 10 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: 52 percent / NH₃ / methanol / 72 h / Ambient temperature

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

9: 96 percent / 2N aq. H₂SO₄ / tetrahydrofuran / Ambient temperature

10: 63 percent / Jones reagent / acetone / 2 h / 0 - 20 °C

With jones reagent; sulfuric acid; 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 tetrahydrofuran; methanol; dichloromethane; acetone;

DOI:10.1021/ja961887v

Reference yield:

(S)-7-(1-Chloro-cyclohexyl)-3-hydroxymethyl-hexahydro-indolizin-5-one → (3S,8aS)-7-Cyclohexyl-5-oxo-6-[((S)-5-oxo-pyrrolidine-2-carbonyl)-amino]-1,2,3,5,8,8a-hexahydro-indolizine-3-carboxylic acid (183593-59-1)

Guidance literature:

Multi-step reaction with 7 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: 52 percent / NH₃ / methanol / 72 h / Ambient temperature

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

6: 96 percent / 2N aq. H₂SO₄ / tetrahydrofuran / Ambient temperature

7: 63 percent / Jones reagent / acetone / 2 h / 0 - 20 °C

With jones reagent; sulfuric acid; 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 tetrahydrofuran; methanol; dichloromethane; acetone;

DOI:10.1021/ja961887v

upstream raw materials:

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

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

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

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