ethyl 2-(4-methoxybenzylamino)-2-cyanoacetate

Base Information

• Chemical Name: ethyl 2-(4-methoxybenzylamino)-2-cyanoacetate
• CAS No.: 895579-15-4
• Molecular Formula: C₁₃H₁₆N₂O₃
• Molecular Weight: 248.282
• Mol file: 895579-15-4.mol

Synonyms:ethyl 2-(4-methoxybenzylamino)-2-cyanoacetate

Chemical Property of ethyl 2-(4-methoxybenzylamino)-2-cyanoacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2-(4-methoxybenzylamino)-2-cyanoacetate

There total 1 articles about ethyl 2-(4-methoxybenzylamino)-2-cyanoacetate 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: 62.0%

1-cyano-2-ethoxy-2-oxoethanaminium 4-methylbenzenesulfonate (37842-58-3) + 4-methoxy-benzaldehyde (123-11-5) → ethyl 2-(4-methoxybenzylamino)-2-cyanoacetate (895579-15-4)

Guidance literature:

1-cyano-2-ethoxy-2-oxoethanaminium 4-methylbenzenesulfonate; 4-methoxy-benzaldehyde; In dichloromethane; at 50 ℃; for 9.5h;

With sodium tris(acetoxy)borohydride; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/ja061970a

Reference yield:

ethyl 2-(4-methoxybenzylamino)-2-cyanoacetate (895579-15-4) → (3S,4S,7R,8R)-8-Hydroxy-3-isopropyl-5-(4-methoxy-benzyl)-7-methyl-2-oxa-5-aza-spiro[3.4]octane-1,6-dione (895579-29-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: (S,S)-[(salen)Al]O / cyclohexane; 2-methyl-propan-2-ol / 120 h / 23 °C

2.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C

2.2: tetrahydrofuran / 4 h / -78 - 0 °C

3.1: sodium borohydride / methanol / 6 h / 0 °C

4.1: Dess-Martin periodinane / pyridine / 1.5 h / 20 °C

5.1: tetrahydrofuran / 4 h / -78 °C

6.1: Red-Al(R) / toluene / 3 h / -78 - 0 °C

7.1: sodium phosphate; sodium chlorite; 2-methyl-2-butene / 2-methyl-propan-2-ol / 0.58 h / 20 °C

8.1: 245 mg / potassium hydrogencarbonate; potassium fluoride; aq. hydrogen peroxide / dimethylformamide / 11 h / 20 °C

9.1: 94 percent / H₂ / Pd/C / methanol; acetic acid / 2 h

10.1: pyridine; methanesulfonyl chloride / CH₂Cl₂ / 19 h / 20 °C

10.2: 75 percent / aq. HCl / CH₂Cl₂

With pyridine; potassium fluoride; sodium chlorite; sodium tetrahydroborate; 2-methyl-but-2-ene; hydrogen; dihydrogen peroxide; potassium hydrogencarbonate; Dess-Martin periodane; methanesulfonyl chloride; sodium bis(2-methoxyethoxy)aluminium dihydride; sodium phosphate; lithium hexamethyldisilazane; palladium on activated charcoal; [((S,S)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine(-2H))Al]2O; In tetrahydrofuran; pyridine; methanol; dichloromethane; cyclohexane; acetic acid; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

DOI:10.1021/ja061970a

Reference yield:

ethyl 2-(4-methoxybenzylamino)-2-cyanoacetate (895579-15-4) → (3S,4S,7R,8S)-8-Hydroxy-3-isopropyl-5-(4-methoxy-benzyl)-7-methyl-2-oxa-5-aza-spiro[3.4]octane-1,6-dione (895579-28-9)

Guidance literature:

Multi-step reaction with 11 steps

1.1: (S,S)-[(salen)Al]O / cyclohexane; 2-methyl-propan-2-ol / 120 h / 23 °C

2.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C

2.2: tetrahydrofuran / 4 h / -78 - 0 °C

3.1: sodium borohydride / methanol / 6 h / 0 °C

4.1: Dess-Martin periodinane / pyridine / 1.5 h / 20 °C

5.1: tetrahydrofuran / 4 h / -78 °C

6.1: Red-Al(R) / toluene / 3 h / -78 - 0 °C

7.1: sodium phosphate; sodium chlorite; 2-methyl-2-butene / 2-methyl-propan-2-ol / 0.58 h / 20 °C

8.1: 245 mg / potassium hydrogencarbonate; potassium fluoride; aq. hydrogen peroxide / dimethylformamide / 11 h / 20 °C

9.1: 94 percent / H₂ / Pd/C / methanol; acetic acid / 2 h

10.1: DMAP; pyridine / 11 h / 0 °C

11.1: 80 percent / sodium nitrite / dimethylformamide / 1.5 h / 20 °C

With pyridine; dmap; potassium fluoride; sodium chlorite; sodium tetrahydroborate; 2-methyl-but-2-ene; hydrogen; dihydrogen peroxide; potassium hydrogencarbonate; Dess-Martin periodane; sodium bis(2-methoxyethoxy)aluminium dihydride; sodium phosphate; lithium hexamethyldisilazane; sodium nitrite; palladium on activated charcoal; [((S,S)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine(-2H))Al]2O; In tetrahydrofuran; pyridine; methanol; cyclohexane; acetic acid; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

DOI:10.1021/ja061970a

upstream raw materials:

1-cyano-2-ethoxy-2-oxoethanaminium 4-methylbenzenesulfonate

4-methoxy-benzaldehyde

Downstream raw materials:

(2R,3R)-ethyl 1-(4-methoxybenzyl)-3-(allyldimethylsilyl)-2-cyano-5-oxopyrrolidine-2-carboxylate

(3S,4S,7R,8R)-8-Hydroxy-3-isopropyl-5-(4-methoxy-benzyl)-7-methyl-2-oxa-5-aza-spiro[3.4]octane-1,6-dione

(3S,4S,7R,8S)-8-Hydroxy-3-isopropyl-5-(4-methoxy-benzyl)-7-methyl-2-oxa-5-aza-spiro[3.4]octane-1,6-dione

(2R,3R,4R)-3-Hydroxy-2-((S)-1-hydroxy-2-methyl-propyl)-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid