(3R,5S,8aR)-3-butyl-5-propyloctahydroindolidine

Base Information

• Chemical Name: (3R,5S,8aR)-3-butyl-5-propyloctahydroindolidine
• CAS No.: 943979-38-2
• Molecular Formula: C₁₅H₂₉N
• Molecular Weight: 223.402
• Mol file: 943979-38-2.mol

Synonyms:

Chemical Property of (3R,5S,8aR)-3-butyl-5-propyloctahydroindolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5S,8aR)-3-butyl-5-propyloctahydroindolidine

There total 24 articles about (3R,5S,8aR)-3-butyl-5-propyloctahydroindolidine 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: 80.0%

(2R,5R)-N-<(benzyloxy)carbonyl>-5-butyl-2-(4-oxoheptyl)pyrrolidine (142841-61-0) → (-)-indolizidine 223AB (67217-85-0,72120-43-5) + (3R,5S,8aR)-3-butyl-5-propyloctahydroindolidine (943979-38-2,72120-43-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; under 760 Torr; Yields of byproduct given;

DOI:10.1021/jo00045a034

Reference yield:

(2R,5R)-N-<(benzyloxy)carbonyl>-2-(4-hydroxyheptyl)-5-butylpyrrolidine (142841-60-9) → (3R,5S,8aR)-3-butyl-5-propyloctahydroindolidine (943979-38-2,72120-43-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / pyridinium dichromate / CH₂Cl₂ / 30 h / 20 °C

2: H₂ / 10 percent Pd/C / methanol

With dipyridinium dichromate; hydrogen; palladium on activated charcoal; In methanol; dichloromethane; 1: Oxidation / 2: Cyclization;

DOI:10.1016/S0040-4020(98)00498-0

Reference yield:

(5S,8S)-12-(Benzyloxy)-5,8-bis<(tert-butyldimethylsilyl)oxy>-1-dodecanol (131618-40-1) → (3R,5S,8aR)-3-butyl-5-propyloctahydroindolidine (943979-38-2,72120-43-5)

Guidance literature:

Multi-step reaction with 15 steps

1: 100 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h / Ambient temperature

2: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature

3: thionyl chloride, triethylamine / CH₂Cl₂ / 0.08 h / Ambient temperature

4: RuCl₃*H₂O, NaIO₄ / CCl₄; acetonitrile; H₂O / 1 h / 0 °C

6: 20percent aq. K₂CO₃ / CH₂Cl₂ / 0.25 h / ice bath

7: 97 percent / 1percent methanolic KOH / methanol / 0.5 h / Ambient temperature

8: 84 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h

9: 81 percent / LiAlH₄ / tetrahydrofuran / 2 h / Ambient temperature

10: H₂, conc. HCl / 10percent Pd-C / methanol / 1 h / 760 Torr

11: 20percent aq. KOH / CHCl₃ / 0.33 h / ice cooling

12: 61 percent / pyridinium dichromate / CH₂Cl₂ / 24 h / Ambient temperature

13: 88 percent / tetrahydrofuran / 0 °C

14: 80 percent / pyridinium dichromate / CH₂Cl₂ / Ambient temperature

15: H₂ / 10percent Pd-C / methanol / 760 Torr

With hydrogenchloride; dmap; ruthenium trichloride; potassium hydroxide; sodium periodate; lithium aluminium tetrahydride; dipyridinium dichromate; thionyl chloride; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; chloroform; water; acetonitrile;

DOI:10.1021/jo00045a034

upstream raw materials:

(2R,5R)-N-<(benzyloxy)carbonyl>-5-butyl-2-(4-oxoheptyl)pyrrolidine

4-penten-1-yllithium

N-carbobenzyloxy-L-proline methyl ester

(5S)-2-Methoxy-1-[(benzyloxy)carbonyl]-5-methoxycarbonylpyrrolidine