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

Base Information

• Chemical Name: (2R,5R)-N-<(benzyloxy)carbonyl>-5-butyl-2-(4-oxobutyl)pyrrolidine
• CAS No.: 142841-56-3
• Molecular Formula: C₂₀H₂₉NO₃
• Molecular Weight: 331.455
• Mol file: 142841-56-3.mol

Synonyms:(2R,5R)-N-<(benzyloxy)carbonyl>-5-butyl-2-(4-oxobutyl)pyrrolidine

Chemical Property of (2R,5R)-N-<(benzyloxy)carbonyl>-5-butyl-2-(4-oxobutyl)pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,5R)-N-<(benzyloxy)carbonyl>-5-butyl-2-(4-oxobutyl)pyrrolidine

There total 12 articles about (2R,5R)-N-<(benzyloxy)carbonyl>-5-butyl-2-(4-oxobutyl)pyrrolidine 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: 61.0%

(2R,5R)-N-<(benzyloxy)carbonyl>-5-butyl-2-(4-hydroxybutyl)pyrrolidine (142841-55-2) → (2R,5R)-N-<(benzyloxy)carbonyl>-5-butyl-2-(4-oxobutyl)pyrrolidine (142841-56-3)

Guidance literature:

With dipyridinium dichromate; In dichloromethane; for 24h; Ambient temperature;

DOI:10.1021/jo00045a034

Reference yield:

(5S,8S)-12-(Benzyloxy)-5,8-bis<(tert-butyldimethylsilyl)oxy>-1-dodecanol (131618-40-1) → (2R,5R)-N-<(benzyloxy)carbonyl>-5-butyl-2-(4-oxobutyl)pyrrolidine (142841-56-3)

Guidance literature:

Multi-step reaction with 12 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

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

Reference yield:

(5S,8S)-1-(benzoyloxy)-12-(benzyloxy)-5,8-dodecanediol (134822-20-1) → (2R,5R)-N-<(benzyloxy)carbonyl>-5-butyl-2-(4-oxobutyl)pyrrolidine (142841-56-3)

Guidance literature:

Multi-step reaction with 10 steps

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

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

4: 20percent aq. K₂CO₃ / CH₂Cl₂ / 0.25 h / ice bath

5: 97 percent / 1percent methanolic KOH / methanol / 0.5 h / Ambient temperature

6: 84 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h

7: 81 percent / LiAlH₄ / tetrahydrofuran / 2 h / Ambient temperature

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

9: 20percent aq. KOH / CHCl₃ / 0.33 h / ice cooling

10: 61 percent / pyridinium dichromate / CH₂Cl₂ / 24 h / Ambient temperature

With hydrogenchloride; dmap; ruthenium trichloride; potassium hydroxide; sodium periodate; lithium aluminium tetrahydride; dipyridinium dichromate; thionyl chloride; 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-hydroxybutyl)pyrrolidine

(5S,8S)-12-(Benzyloxy)-5,8-bis<(tert-butyldimethylsilyl)oxy>-1-dodecanol

(2R,5R)-2-<4-(benzoyloxy)butyl>-5-<4-(benzyloxy)butyl>pyrrolidine

(5S,8S)-1-(benzoyloxy)-12-(benzyloxy)-5,8-dodecanediol

Downstream raw materials:

(2R,5R)-N-<(benzyloxy)carbonyl>-2-<7-(benzyloxy)-4-oxoheptyl>-5-butylpyrrolidine

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

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

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