Methyl 1-(N-benzylamino)-2,2-dimethylcyclopropanecarboxylic ester

Base Information

• Chemical Name: Methyl 1-(N-benzylamino)-2,2-dimethylcyclopropanecarboxylic ester
• CAS No.: 160194-12-7
• Molecular Formula: C₁₄H₁₉NO₂
• Molecular Weight: 233.31
• Mol file: 160194-12-7.mol

Synonyms:Methyl 1-(N-benzylamino)-2,2-dimethylcyclopropanecarboxylic ester

Chemical Property of Methyl 1-(N-benzylamino)-2,2-dimethylcyclopropanecarboxylic ester

Chemical Property:

Purity/Quality:

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MSDS Files:

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Technology Process of Methyl 1-(N-benzylamino)-2,2-dimethylcyclopropanecarboxylic ester

There total 15 articles about Methyl 1-(N-benzylamino)-2,2-dimethylcyclopropanecarboxylic 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: 78.0%

2-Benzylamino-4-chloro-3,3-dimethyl-butyric acid methyl ester (160194-14-9) → Methyl 1-(N-benzylamino)-2,2-dimethylcyclopropanecarboxylic ester (160194-12-7)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; for 1h; Heating;

DOI:10.1021/jo00102a022

Reference yield:

3-methyl-butan-2-one (563-80-4) → Methyl 1-(N-benzylamino)-2,2-dimethylcyclopropanecarboxylic ester (160194-12-7)

Guidance literature:

Multi-step reaction with 12 steps

1: 7 h / Heating

2: 15percent aq. NaHCO₃ / 24 h / Ambient temperature

3: 87 percent / pyridine / CH₂Cl₂ / 24 h / Ambient temperature

4: 82 percent / LiCl / dimethylformamide / 15 h / Heating

5: 8 percent / Br₂ / CH₂Cl₂ / 1 h / Ambient temperature

6: NaOMe / 1.) MeOH, ice-cooling, 5 min, 2.) r.t., 1 h

7: 90 percent / SO₂Cl₂

8: 60 percent / Ag₂CO₃ / 17 h / Heating

9: 94 percent / p-TsOH / CH₂Cl₂; H₂O / 2 h / Heating

10: 80 percent / TiCl₄ / diethyl ether; pentane / 2 h / Ambient temperature

11: 66 percent / NaCNBH₃, 98percent AcOH / methanol / 1 h / 0 °C

12: 78 percent / t-BuOK / tetrahydrofuran / 1 h / Heating

With pyridine; sulfuryl dichloride; potassium tert-butylate; bromine; sodium methylate; titanium tetrachloride; sodium cyanoborohydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; acetic acid; silver carbonate; lithium chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; pentane;

DOI:10.1021/jo00102a022

Reference yield:

3,3-dimethyl-4-[(methylsulphonyl)oxy]-2-butanone (4301-02-4) → Methyl 1-(N-benzylamino)-2,2-dimethylcyclopropanecarboxylic ester (160194-12-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 82 percent / LiCl / dimethylformamide / 15 h / Heating

2: 8 percent / Br₂ / CH₂Cl₂ / 1 h / Ambient temperature

3: NaOMe / 1.) MeOH, ice-cooling, 5 min, 2.) r.t., 1 h

4: 90 percent / SO₂Cl₂

5: 60 percent / Ag₂CO₃ / 17 h / Heating

6: 94 percent / p-TsOH / CH₂Cl₂; H₂O / 2 h / Heating

7: 80 percent / TiCl₄ / diethyl ether; pentane / 2 h / Ambient temperature

8: 66 percent / NaCNBH₃, 98percent AcOH / methanol / 1 h / 0 °C

9: 78 percent / t-BuOK / tetrahydrofuran / 1 h / Heating

With sulfuryl dichloride; potassium tert-butylate; bromine; sodium methylate; titanium tetrachloride; sodium cyanoborohydride; toluene-4-sulfonic acid; acetic acid; silver carbonate; lithium chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; pentane;

DOI:10.1021/jo00102a022

upstream raw materials:

2-Benzylamino-4-chloro-3,3-dimethyl-butyric acid methyl ester

3-methyl-butan-2-one

3,3-dimethyl-4-[(methylsulphonyl)oxy]-2-butanone

2,2-Dimethyl-3-oxo-1-butyl trifluoroacetate