1-[(Benzyloxy)carbonyl]-3-methylpyrrolidine-3-carboxylic acid

Base Information

• Chemical Name: 1-[(Benzyloxy)carbonyl]-3-methylpyrrolidine-3-carboxylic acid
• CAS No.: 1412254-20-6
• Molecular Formula: C14H17NO4
• Molecular Weight: 263.28908
• Mol file: 1412254-20-6.mol

Synonyms:1-[(BENZYLOXY)CARBONYL]-3-METHYLPYRROLIDINE-3-CARBOXYLIC ACID;(S)-3-Methyl-pyrrolidine-1,3-dicarboxylic acid 1-benzyl ester;(S)-1-((benzyloxy)carbonyl)-3-methylpyrrolidine-3-carboxylic acid;(3S)-1-[(Benzyloxy)carbonyl]-3-methyl-3-pyrrolidinecarboxylic acid;1,3-Pyrrolidinedicarboxylic acid, 3-methyl-, 1-(phenylmethyl) ester, (3S)-

Chemical Property of 1-[(Benzyloxy)carbonyl]-3-methylpyrrolidine-3-carboxylic acid

Chemical Property:

• Boiling Point: 427.5±45.0 °C(Predicted)
• PKA: 4.63±0.20(Predicted)
• PSA: 66.84000
• Density: 1.261±0.06 g/cm3(Predicted)
• LogP: 2.05770

Purity/Quality:

99% ^*data from raw suppliers

(S)-3-Methyl-Pyrrolidine-1,3-DicarboxylicAcid1-BenzylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[(Benzyloxy)carbonyl]-3-methylpyrrolidine-3-carboxylic acid

There total 9 articles about 1-[(Benzyloxy)carbonyl]-3-methylpyrrolidine-3-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: 99.0%

1-benzyl 3-methyl 3-methylpyrrolidine-1,3-dicarboxylate (912444-74-7) → 1-((benzyloxy)carbonyl)-3-methylpyrrolidine-3-carboxylic acid (912444-75-8,1412254-20-6)

Guidance literature:

1-benzyl 3-methyl 3-methylpyrrolidine-1,3-dicarboxylate; With water; lithium hydroxide; In ethanol; for 1h; Heating;

With potassium hydrogensulfate; In water; pH=3 - 4;

Reference yield: 97.0%

C18H25NO4 (1446482-09-2) → 1-((benzyloxy)carbonyl)-3-methylpyrrolidine-3-carboxylic acid (912444-75-8,1412254-20-6)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 17h;

DOI:10.1021/jo4010316

Reference yield:

pyrrolidine-1,3-dicarboxylic acid 1-benzyl ester 3-methyl ester (188847-00-9,1217655-90-7) → 1-((benzyloxy)carbonyl)-3-methylpyrrolidine-3-carboxylic acid (912444-75-8,1412254-20-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.33 h / -78 °C

1.2: -78 - 20 °C

2.1: water; lithium hydroxide / ethanol / 1 h / Heating

2.2: pH 3 - 4

With water; lithium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol;

upstream raw materials:

1-benzyl 3-methyl 3-methylpyrrolidine-1,3-dicarboxylate

1-tert-butyl 4-ethyl 2-cyano-2-methylbutanedioate

C₁₀H₁₇NO₃

C₁₀H₁₉NO₂

Downstream raw materials:

3-methylpyrrolidine-3-carboxylic acid

3-tert-butoxycarbonylamino-3-methyl-pyrrolidine

Refernces

• 1、 Nagata, Kazuhiro,Kuga, Yasushi,Higashi, Akinori,Kinoshita, Atsushi,Kanemitsu, Takuya,Miyazaki, Michiko,Itoh, Takashi. "Asymmetric synthesis and catalytic activity of 3-methyl-β-proline in enantioselective anti -mannich-type reactions". . p. 7131 - 7136. Retrieved 2013/08/23.
• 2、 -. "1H-benzimidazole-4-carboxamides substituted with a quaternary carbon at the 2-position are potent PARP inhibitors". Page/Page column 16. . Retrieved 2008/06/13.