2-[(R)-1-Benzyl-5-tert-butoxycarbonyl-pyrrolidin-(2Z)-ylidene]-succinic acid dibenzyl ester

Base Information

• Chemical Name: 2-[(R)-1-Benzyl-5-tert-butoxycarbonyl-pyrrolidin-(2Z)-ylidene]-succinic acid dibenzyl ester
• CAS No.: 208037-71-2
• Molecular Formula: C₃₄H₃₇NO₆
• Molecular Weight: 555.671
• Mol file: 208037-71-2.mol

Synonyms:2-[(R)-1-Benzyl-5-tert-butoxycarbonyl-pyrrolidin-(2Z)-ylidene]-succinic acid dibenzyl ester

Chemical Property of 2-[(R)-1-Benzyl-5-tert-butoxycarbonyl-pyrrolidin-(2Z)-ylidene]-succinic acid dibenzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(R)-1-Benzyl-5-tert-butoxycarbonyl-pyrrolidin-(2Z)-ylidene]-succinic acid dibenzyl ester

There total 3 articles about 2-[(R)-1-Benzyl-5-tert-butoxycarbonyl-pyrrolidin-(2Z)-ylidene]-succinic acid dibenzyl 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:

dibenzyl 2-hydroxysuccinate (56977-10-7) → 2-[(R)-1-Benzyl-5-tert-butoxycarbonyl-pyrrolidin-(2Z)-ylidene]-succinic acid dibenzyl ester (208037-71-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 2,6-lutidine / CH₂Cl₂ / 2.75 h / -10 - -5 °C

2: 2.) PPh₃, 3.) N-methylpiperidine / 1.) MeCN, room temperature, 24 h, 2.) room temperature, 1 h, 3.) -3 deg C, 14 h

With 2,6-dimethylpyridine; N-methylcyclohexylamine; triphenylphosphine; In dichloromethane;

DOI:10.1021/jo980153t

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → 2-[(R)-1-Benzyl-5-tert-butoxycarbonyl-pyrrolidin-(2Z)-ylidene]-succinic acid dibenzyl ester (208037-71-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / p-TsOH*H₂O / benzene / 4 h / Heating

2: 2,6-lutidine / CH₂Cl₂ / 2.75 h / -10 - -5 °C

3: 2.) PPh₃, 3.) N-methylpiperidine / 1.) MeCN, room temperature, 24 h, 2.) room temperature, 1 h, 3.) -3 deg C, 14 h

With 2,6-dimethylpyridine; N-methylcyclohexylamine; toluene-4-sulfonic acid; triphenylphosphine; In dichloromethane; benzene;

DOI:10.1021/jo980153t

Reference yield:

(R)-1-benzyl-5-thioxoproline tert-butyl ester (90741-32-5) + 2-Trifluoromethanesulfonyloxy-succinic acid dibenzyl ester (208037-70-1) → 2-[(R)-1-Benzyl-5-tert-butoxycarbonyl-pyrrolidin-(2Z)-ylidene]-succinic acid dibenzyl ester (208037-71-2)

Guidance literature:

With N-methylcyclohexylamine; triphenylphosphine; Yield given. Multistep reaction; 1.) MeCN, room temperature, 24 h, 2.) room temperature, 1 h, 3.) -3 deg C, 14 h;

DOI:10.1021/jo980153t

upstream raw materials:

(R)-1-benzyl-5-thioxoproline tert-butyl ester

2-Trifluoromethanesulfonyloxy-succinic acid dibenzyl ester

dibenzyl 2-hydroxysuccinate

benzyl alcohol

Downstream raw materials:

Cocaine

benzylecgonine

(1R,5S)-8-(tert-butyloxycarbonyl)-8-azabicyclo[3.2.1]-2-octanone p-tosylhydrazone

(1R,2R,3S,5S)-3-Benzoyloxy-2-carbamoyl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester