methyl 4-formyl-2,3-dihydro-1H-pyrrole-2-carboxylate

Base Information

• Chemical Name: methyl 4-formyl-2,3-dihydro-1H-pyrrole-2-carboxylate
• CAS No.: 222420-87-3
• Molecular Formula: C₇H₉NO₃
• Molecular Weight: 155.153
• DSSTox Substance ID: DTXSID10572703
• Nikkaji Number: J1.049.379J
• Mol file: 222420-87-3.mol

Synonyms:222420-87-3;methyl 4-formyl-2,3-dihydro-1H-pyrrole-2-carboxylate;DTXSID10572703

Chemical Property of methyl 4-formyl-2,3-dihydro-1H-pyrrole-2-carboxylate

Chemical Property:

• PSA: 55.40000
• LogP: -0.06710
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 155.058243149
• Heavy Atom Count: 11
• Complexity: 210

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CC(=CN1)C=O

Technology Process of methyl 4-formyl-2,3-dihydro-1H-pyrrole-2-carboxylate

There total 1 articles about methyl 4-formyl-2,3-dihydro-1H-pyrrole-2-carboxylate 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: 73.0%

isocyanoacetic acid methyl ester (39687-95-1) + acrolein (107-02-8,25068-14-8) → (+/-)-methyl 4-formyl-2,3-dihydro-1H-pyrrole-2-carboxylate (222420-87-3)

Guidance literature:

With silver(I) acetate; In acetonitrile; at 20 - 22 ℃; for 4h;

DOI:10.1016/S0040-4020(98)01216-2

Reference yield:

(+/-)-methyl 4-formyl-2,3-dihydro-1H-pyrrole-2-carboxylate (222420-87-3) → 2-[(4-benzoyloxymethyl-1-tert-butoxycarbonyl-2,3-dihydro-1H-pyrrole-2-carbonyl)-(2,5-dimethoxybenzyl)amino]malonic acid diethyl ester

Guidance literature:

Multi-step reaction with 9 steps

1.1: 66 percent / DMAP / CH₂Cl₂ / 10 h / 20 °C

2.1: 99 percent / NaBH₄ / CH₂Cl₂; methanol / 2 h / -78 - 0 °C

3.1: 83 percent / triethylamine; DMAP / CH₂Cl₂ / 10 h / 20 °C

4.1: 68 percent / LiOH / methanol; H₂O / 10 h / 20 °C

5.1: 64 percent / 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one; triethylamine / CH₂Cl₂ / 4 h / 20 °C

6.1: LHMDS / diethyl ether; tetrahydrofuran / 1 h / -78 °C

6.2: 88 percent / diethyl ether; tetrahydrofuran / 7 h / -78 °C

7.1: 89 percent / TBAF / tetrahydrofuran / 10 h / 20 °C

8.1: 70 percent / DMAP; pyridine / CH₂Cl₂ / 3 h / 20 °C

9.1: 94 percent / DBU / Pd₂(dba)3 / tetrahydrofuran / 0.33 h / 65 °C

With pyridine; dmap; lithium hydroxide; sodium tetrahydroborate; tetrabutyl ammonium fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; lithium hexamethyldisilazane; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; 9.1: Heck reaction;

DOI:10.1016/j.tet.2006.06.114

Reference yield:

(+/-)-methyl 4-formyl-2,3-dihydro-1H-pyrrole-2-carboxylate (222420-87-3) → 3-benzyl-7-methylene-4-oxo-3,8-diazabicyclo[3.2.1]octane-2,2,8-tricarboxylic acid 8-tert-butyl ester 2,2-diethyl ester

Guidance literature:

Multi-step reaction with 9 steps

1.1: 66 percent / DMAP / CH₂Cl₂ / 10 h / 20 °C

2.1: 99 percent / NaBH₄ / CH₂Cl₂; methanol / 2 h / -78 - 0 °C

3.1: 83 percent / triethylamine; DMAP / CH₂Cl₂ / 10 h / 20 °C

4.1: 68 percent / LiOH / methanol; H₂O / 10 h / 20 °C

5.1: 78 percent / 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one; triethylamine / CH₂Cl₂ / 4 h / 20 °C

6.1: LHMDS / diethyl ether; tetrahydrofuran / 1 h / -78 °C

6.2: 76 percent / diethyl ether; tetrahydrofuran / 7 h / -78 °C

7.1: 92 percent / TBAF / tetrahydrofuran / 10 h / 20 °C

8.1: 76 percent / DMAP; pyridine / CH₂Cl₂ / 3 h / 20 °C

9.1: 96 percent / DBU / Pd₂(dba)3 / tetrahydrofuran / 0.33 h / 65 °C

With pyridine; dmap; lithium hydroxide; sodium tetrahydroborate; tetrabutyl ammonium fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; lithium hexamethyldisilazane; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; 9.1: Heck reaction;

DOI:10.1016/j.tet.2006.06.114

upstream raw materials:

isocyanoacetic acid methyl ester

acrolein

Downstream raw materials:

2-[benzyl-(1-tert-butoxycarbonyl-4-hydroxymethyl-2,3-dihydro-1H-pyrrole-2-carbonyl)amino]-malonic acid diethyl ester

2-[(4-benzoyloxymethyl-1-tert-butoxycarbonyl-2,3-dihydro-1H-pyrrole-2-carbonyl)-methyl-amino]-malonic acid diethyl ester

2-(benzyl-ethoxycarbonylmethyl-carbamoyl)-4-(tert-butyldimethylsilanyloxymethyl)-2,3-dihydropyrrole-1-carboxylic acid tert-butyl ester

2-[(1-tert-butoxycarbonyl-4-hydroxymethyl-2,3-dihydro-1H-pyrrole-2-carbonyl)-(2,5-dimethoxybenzyl)-amino]malonic acid diethyl ester