1-Pyrrolidinecarboxylic acid, 2-butyl-5-(4-hydroxyheptyl)-, phenylmethyl ester

Base Information

• Chemical Name: 1-Pyrrolidinecarboxylic acid, 2-butyl-5-(4-hydroxyheptyl)-, phenylmethyl ester
• CAS No.: 142841-60-9
• Molecular Formula: C23H37NO3
• Molecular Weight: 375.552
• Mol file: 142841-60-9.mol

Synonyms:

Chemical Property of 1-Pyrrolidinecarboxylic acid, 2-butyl-5-(4-hydroxyheptyl)-, phenylmethyl ester

Chemical Property:

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-Pyrrolidinecarboxylic acid, 2-butyl-5-(4-hydroxyheptyl)-, phenylmethyl ester

There total 34 articles about 1-Pyrrolidinecarboxylic acid, 2-butyl-5-(4-hydroxyheptyl)-, phenylmethyl ester 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: 88.0%

n-propylmagnesium bromide (927-77-5) + (2R,5R)-N-<(benzyloxy)carbonyl>-5-butyl-2-(4-oxobutyl)pyrrolidine (142841-56-3) → (2R,5R)-N-<(benzyloxy)carbonyl>-2-(4-hydroxyheptyl)-5-butylpyrrolidine (142841-60-9)

Guidance literature:

In tetrahydrofuran; at 0 ℃;

DOI:10.1021/jo00045a034

Reference yield: 73.0%

ethylmagnesium bromide (925-90-6) + (2R,5R)-1-[(Benzyloxy)carbonyl]-2-butyl-5-(4,5-epoxypentyl)pyrrolidine (214072-11-4) → (2R,5R)-N-<(benzyloxy)carbonyl>-2-(4-hydroxyheptyl)-5-butylpyrrolidine (142841-60-9)

Guidance literature:

With copper(l) iodide; In diethyl ether; at -15 ℃; for 2h;

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

Reference yield:

(5R,8R)-5,8-Bis<(tert-butyldimethylsilyl)oxy>-1,12-dodecanediol (131618-30-9) → (2S,5S)-N-<(benzyloxy)carbonyl>-2-(hydroxyheptyl)-5-butylpyrrolidine (142841-60-9)

Guidance literature:

Multi-step reaction with 11 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

With dmap; ruthenium trichloride; sodium hydroxide; sodium periodate; 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:

n-propylmagnesium bromide

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

ethylmagnesium bromide

(2R,5R)-1-[(Benzyloxy)carbonyl]-2-butyl-5-(4,5-epoxypentyl)pyrrolidine

Downstream raw materials:

(-)-indolizidine 223AB

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

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