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

Base Information

• Chemical Name: (3S,5R,8aS)-3-butyl-5-propyloctahydroindolidine
• CAS No.: 83024-11-7
• Molecular Formula: C₁₅H₂₉N
• Molecular Weight: 223.402
• Mol file: 83024-11-7.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 17 articles about (3S,5R,8aS)-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: 38.0%

(3R,8aR)-3-Butyl-5-propyl-3,5,6,7,8,8a-hexahydro-indolizine (72049-65-1,72074-83-0) → (3R,8aR)-3-Butyl-5-propyl-octahydro-indolizine (67217-85-0,81076-50-8,81076-51-9,81076-52-0,81076-53-1,83024-10-6,83024-11-7,96894-83-6,142925-68-6,150134-99-9,72120-43-5)

Guidance literature:

With hydrogen; platinum(IV) oxide; In acetic acid;

DOI:10.1021/jo01289a049

Reference yield:

(2S,5S)-N-<(benzyloxy)carbonyl>-5-butyl-2-(4-oxoheptyl)pyrrolidine (142841-61-0) → (3S,5R,8aS)-3-butyl-5-propyloctahydroindolidine (67217-85-0,81076-50-8,81076-51-9,81076-52-0,81076-53-1,83024-10-6,83024-11-7,96894-83-6,142925-68-6,150134-99-9,72120-43-5) + indolizidine 223AB (142925-68-6,72120-43-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; under 760 Torr;

DOI:10.1021/jo00045a034

Reference yield:

(5R,8R)-5,8-Bis<(tert-butyldimethylsilyl)oxy>-1,12-dodecanediol (131618-30-9) → (3S,5R,8aS)-3-butyl-5-propyloctahydroindolidine (67217-85-0,81076-50-8,81076-51-9,81076-52-0,81076-53-1,83024-10-6,83024-11-7,96894-83-6,142925-68-6,150134-99-9,72120-43-5)

Guidance literature:

Multi-step reaction with 13 steps

1: 46 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 1.5 h / Ambient temperature

2: 92 percent / CBr₄, triphenylphosphine / CH₂Cl₂ / 0.17 h / 0 °C

3: 84 percent / triethylamine, H₂ / 10percent Pd-C / methanol / 1 h / 760 Torr

4: 91 percent / 1 M tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

5: thionyl chloride, triethylamine / CH₂Cl₂ / Ambient temperature

6: RuCl₃*H₂O, NaIO₄ / CCl₄; acetonitrile; H₂O / 2 h / 0 °C

8: 20percent aq. K₂CO₃ / CH₂Cl₂ / ice bath

9: 90 percent / 15percent aq. NaOH / tetrahydrofuran; methanol / 2 h / Ambient temperature

10: 1) oxalyl chloride, DMSO; 2b) triethylamine / 1) CH₂Cl₂, -78 deg C, 30 min; 2) CH₂Cl₂, a) -78 deg C, 1 h, b) triethylamine, room temperature, 15 min

11: tetrahydrofuran / 0 °C

12: pyridinium dichromate / CH₂Cl₂ / Ambient temperature

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

With dmap; ruthenium trichloride; sodium hydroxide; sodium periodate; dipyridinium dichromate; thionyl chloride; oxalyl dichloride; carbon tetrabromide; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; water; acetonitrile;

DOI:10.1021/jo00045a034

upstream raw materials:

(3R,8aR)-3-Butyl-5-propyl-3,5,6,7,8,8a-hexahydro-indolizine

1-(methoxycarbonyl)-2-n-butyl-3-pyrroline

(2R,5R)-2-(4-Bromo-heptyl)-5-butyl-2,5-dihydro-pyrrole-1-carboxylic acid methyl ester

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