(2S,5S)-5-methylpyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: (2S,5S)-5-methylpyrrolidine-2-carboxylic acid
• CAS No.: 38533-38-9
• Molecular Formula: C₆H₁₁NO₂
• Molecular Weight: 129.16
• Mol file: 38533-38-9.mol

Synonyms:cis-5-methylproline

Chemical Property of (2S,5S)-5-methylpyrrolidine-2-carboxylic acid

Chemical Property:

• PSA: 49.33000
• LogP: 0.54030

Purity/Quality:

98%,99%, ^*data from raw suppliers

(-)-cis-5-Methyl-L-Proline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (-)-cis-5-Methyl-L-Proline is a reagent used in the preparation of Perindopril (P287500), an antihypertensive agent.

Technology Process of (2S,5S)-5-methylpyrrolidine-2-carboxylic acid

There total 19 articles about (2S,5S)-5-methylpyrrolidine-2-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:

methyl 5-oxo-2-[N-(9-(9-phenylfluorenyl))amino]hexanoate (296775-02-5) → cis-5-methylproline (7244-99-7,13532-58-6,13532-74-6,16639-15-9,28115-34-6,38228-16-9,38533-00-5,38533-38-9,49669-55-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / H₂ / Pd/C / methanol / 48 h / 3040 Torr

2: 96 percent / KOSiMe₃ / diethyl ether / 18 h / 20 °C

3: TFA / CH₂Cl₂

With potassium trimethylsilonate; hydrogen; trifluoroacetic acid; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane;

DOI:10.1139/v00-176

Reference yield:

5-oxo-2-(9-phenyl-9H-fluoren-9-ylamino)-hexanoic acid → cis-5-methylproline (7244-99-7,13532-58-6,13532-74-6,16639-15-9,28115-34-6,38228-16-9,38533-00-5,38533-38-9,49669-55-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 259 mg / K₂CO₃ / acetonitrile / 18 h / 20 °C

2: 92 percent / H₂ / Pd/C / methanol / 48 h / 3040 Torr

3: 96 percent / KOSiMe₃ / diethyl ether / 18 h / 20 °C

4: TFA / CH₂Cl₂

With potassium trimethylsilonate; hydrogen; potassium carbonate; trifluoroacetic acid; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane; acetonitrile;

DOI:10.1139/v00-176

Reference yield:

methyl 5-oxo-4-(methyloxycarbonyl)-2-[N-(9-phenylfluoren-9-yl)amino]hexanoate (296774-83-9) → cis-5-methylproline (7244-99-7,13532-58-6,13532-74-6,16639-15-9,28115-34-6,38228-16-9,38533-00-5,38533-38-9,49669-55-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 1N NaOH / ethanol / 5 h / Heating

2: 259 mg / K₂CO₃ / acetonitrile / 18 h / 20 °C

3: 92 percent / H₂ / Pd/C / methanol / 48 h / 3040 Torr

4: 96 percent / KOSiMe₃ / diethyl ether / 18 h / 20 °C

5: TFA / CH₂Cl₂

With sodium hydroxide; potassium trimethylsilonate; hydrogen; potassium carbonate; trifluoroacetic acid; palladium on activated charcoal; In methanol; diethyl ether; ethanol; dichloromethane; acetonitrile;

DOI:10.1139/v00-176

upstream raw materials:

ethyl cis-5-methylpyrrolidine-2-carboxylate

cis-N-(Boc)-5-methylproline

cis-N-(Boc)-5-methylproline methyl ester

methyl 5-oxo-2-[N-(9-(9-phenylfluorenyl))amino]hexanoate

Downstream raw materials:

(2S,5S)-5-methyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

(5S)-1-{[(5R,6S)-5,6-bis(4-chlorophenyl)-3-isopropyl-6-methyl-5,6-dihydroimidazo[2,1-b][1,3]thiazol-2-yl]carbonyl}-N,N,5-trimethyl-L-prolinamide

Refernces

• 1、 Miyazaki, Masaki,Naito, Hiroyuki,Sugimoto, Yuuichi,Yoshida, Keisuke,Kawato, Haruko,Okayama, Tooru,Shimizu, Hironari,Miyazaki, Masaya,Kitagawa, Mayumi,Seki, Takahiko,Fukutake, Setsuko,Shiose, Yoshinobu,Aonuma, Masashi,Soga, Tsunehiko. "Synthesis and evaluation of novel orally active p53-MDM2 interaction inhibitors". . p. 4319 - 4331. Retrieved 2013/07/27.
• 2、 Davis,Zhang,Lee. "Masked oxo sulfinimines (N-sulfinyl imines) in the asymmetric synthesis of proline and pipecolic acid derivatives.". . p. 759 - 762. Retrieved 2007/10/03.