3-(Carboxymethyl)-4-isopropylpyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: 3-(Carboxymethyl)-4-isopropylpyrrolidine-2-carboxylic acid
• CAS No.: 5626-44-8
• Molecular Formula: C₁₀H₁₇NO₄
• Molecular Weight: 215.249
• Mol file: 5626-44-8.mol

Synonyms:alpha-Dihydrokainic acid;3-(carboxymethyl)-4-isopropylpyrrolidine-2-carboxylic acid;FT-0640074

Chemical Property of 3-(Carboxymethyl)-4-isopropylpyrrolidine-2-carboxylic acid

Chemical Property:

• XLogP3: -1.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 215.11575802
• Heavy Atom Count: 15
• Complexity: 264

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)C1CNC(C1CC(=O)O)C(=O)O

Technology Process of 3-(Carboxymethyl)-4-isopropylpyrrolidine-2-carboxylic acid

There total 21 articles about 3-(Carboxymethyl)-4-isopropylpyrrolidine-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:

(2S,3S,4S)-3-Carboxymethyl-4-isopropyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester → (+/-)-α-dihydroallokainic acid (5626-44-8,52497-36-6,92117-73-2,102686-09-9,112572-96-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 11h;

DOI:10.1055/s-2005-868477

Reference yield:

N-Boc-3-(carboxymethyl)-4-(i-propylidene)-2-pyrrolidinecarboxylic acid dimethyl ester → (+/-)-α-dihydroallokainic acid (5626-44-8,52497-36-6,92117-73-2,102686-09-9,112572-96-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / H₂ / PtO₂ / methanol / 14 h / 20 °C / 760 Torr

2: KOH / tetrahydrofuran; H₂O / 15 h / 20 °C

3: 55 mg / TFA / CH₂Cl₂ / 11 h / 20 °C

With potassium hydroxide; hydrogen; trifluoroacetic acid; platinum(IV) oxide; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1021/jo0513865

Reference yield:

(2S,3S)-3-Carboxymethyl-4-isopropylidene-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester → (+/-)-α-dihydroallokainic acid (5626-44-8,52497-36-6,92117-73-2,102686-09-9,112572-96-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 174 mg / toluene; methanol; hexane / 16 h / 20 °C

2: 98 percent / H₂ / PtO₂ / methanol / 14 h / 20 °C / 760 Torr

3: KOH / tetrahydrofuran; H₂O / 15 h / 20 °C

4: 55 mg / TFA / CH₂Cl₂ / 11 h / 20 °C

With potassium hydroxide; hydrogen; trifluoroacetic acid; platinum(IV) oxide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; toluene;

DOI:10.1021/jo0513865

upstream raw materials:

(+/-)-(3,3-dichloro-5t-isopropyl-2-oxo-[4r]piperidyl)-acetic acid ethyl ester

(+/-)-(5t-isopropyl-2-oxo-[4r]piperidyl)-acetic acid ethyl ester

(+/-)-(3ξ-ethoxycarbonyl-5t-isopropyl-2-oxo-[4r]piperidyl)-acetic acid ethyl ester

(+/-)-(1,2t-bis-ethoxycarbonyl-4t-isopropyl-pyrrolidin-3r-yl)-malonic acid diethyl ester