1H-Pyrrole-1,2-dicarboxylic acid, 2,3-dihydro-, 1-(1,1-dimethylethyl) ester, (S)-

Base Information

• Chemical Name: 1H-Pyrrole-1,2-dicarboxylic acid, 2,3-dihydro-, 1-(1,1-dimethylethyl) ester, (S)-
• CAS No.: 90104-21-5
• Molecular Formula: C10H15NO4
• Molecular Weight: 213.233
• Mol file: 90104-21-5.mol

Synonyms:

Chemical Property of 1H-Pyrrole-1,2-dicarboxylic acid, 2,3-dihydro-, 1-(1,1-dimethylethyl) ester, (S)-

Chemical Property:

Purity/Quality:

99.9% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1H-Pyrrole-1,2-dicarboxylic acid, 2,3-dihydro-, 1-(1,1-dimethylethyl) ester, (S)-

There total 1 articles about 1H-Pyrrole-1,2-dicarboxylic acid, 2,3-dihydro-, 1-(1,1-dimethylethyl) ester, (S)- 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:

N-BOC-3,4-didehydro-(S)-proline methyl ester (74844-93-2) + (S)-1-tert-butyl 2-methyl 2,3-dihydro-1H-pyrrole-1,2-dicarboxylate (83548-46-3) + 1-tert-butyl 2-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate (203866-16-4) → 1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrole-2-carboxylic acid (90104-21-5) + (S)-2,5-dihydropyrrole-1,2-dicarboxylic acid 1-tert-butyl ester (51154-06-4) + (2S,4S)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid (203866-13-1)

Guidance literature:

N-BOC-3,4-didehydro-(S)-proline methyl ester; (S)-1-tert-butyl 2-methyl 2,3-dihydro-1H-pyrrole-1,2-dicarboxylate; 1-tert-butyl 2-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate; With sodium hydroxide; water; at 40 ℃; for 2h;

With hydrogenchloride; In water; at 5 ℃; pH=5;

With hydrogenchloride; sodium hydroxide; sodium hypochlorite; more than 3 stages; Product distribution / selectivity;

Reference yield: 90.0%

1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrole-2-carboxylic acid (90104-21-5) → (5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester (709031-38-9)

Guidance literature:

1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrole-2-carboxylic acid; With methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at -25 - -20 ℃; for 2h; Large scale;

With ammonia; In tetrahydrofuran; at 0 - 20 ℃; for 3h; Large scale;

Reference yield: 65.0%

1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrole-2-carboxylic acid (90104-21-5) + 2,3,4,5,6-pentafluorophenol (771-61-9) → 2,3-dihydro-pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-pentafluorophenyl ester (915779-98-5)

Guidance literature:

With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; at 20 ℃; for 4.5h;

DOI:10.1016/j.tet.2006.06.114

upstream raw materials:

N-BOC-3,4-didehydro-(S)-proline methyl ester

(S)-1-tert-butyl 2-methyl 2,3-dihydro-1H-pyrrole-1,2-dicarboxylate

1-tert-butyl 2-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate

Downstream raw materials:

2,3-dihydro-pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-pentafluorophenyl ester

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

3-cyano-(αS)-α-(3-hydroxytricyclo[3.3.1.1^3,7]dec-1-yl)-β-oxo-(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-2-ethanecarbamic acid 1,1-dimethylethyl ester

Saxagliptin hydrochloride

Refernces