Methyl 1-amino-2,2-dimethylcyclopropane-1-carboxylate

Base Information

• Chemical Name: Methyl 1-amino-2,2-dimethylcyclopropane-1-carboxylate
• CAS No.: 159279-77-3
• Molecular Formula: C₇H₁₃NO₂
• Molecular Weight: 143.186
• DSSTox Substance ID: DTXSID80394797
• Mol file: 159279-77-3.mol

Synonyms:159279-77-3;methyl 1-amino-2,2-dimethylcyclopropane-1-carboxylate;METHYL 1-AMINO-2,2-DIMETHYLCYCLOPROPANECARBOXYLATE;SCHEMBL13639011;DTXSID80394797;AKOS006276988;EN300-7113657

Chemical Property of Methyl 1-amino-2,2-dimethylcyclopropane-1-carboxylate

Chemical Property:

• PSA: 52.32000
• LogP: 0.98710
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 143.094628657
• Heavy Atom Count: 10
• Complexity: 176

Purity/Quality:

97% ^*data from raw suppliers

Methyl1-amino-2,2-dimethylcyclopropanecarboxylate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CC1(C(=O)OC)N)C

Technology Process of Methyl 1-amino-2,2-dimethylcyclopropane-1-carboxylate

There total 18 articles about Methyl 1-amino-2,2-dimethylcyclopropane-1-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%

Methyl 1-(N-benzylideneamino)-2,2-dimethylcyclopropanecarboxylic ester → Methyl 1-amino-2,2-dimethylcyclopropanecarboxylic ester (159279-77-3)

Guidance literature:

With oxalic acid; In dichloromethane; water; for 1h; Heating;

DOI:10.1021/jo00102a022

Reference yield:

1-Isocyanato-2,2-dimethyl-cyclopropanecarboxylic acid methyl ester (1026253-32-6) → Methyl 1-amino-2,2-dimethylcyclopropanecarboxylic ester (159279-77-3)

Guidance literature:

With hydrogenchloride; In toluene; at 60 ℃; for 0.5h; Yield given;

DOI:10.1021/jo00105a045

Reference yield:

3-methyl-butan-2-one (563-80-4) → Methyl 1-amino-2,2-dimethylcyclopropanecarboxylic ester (159279-77-3)

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: 95 percent / NaOMe / 2 h / Heating

12: 73 percent / (COOH)2*2H₂O / H₂O; CH₂Cl₂ / 1 h / Heating

With pyridine; sulfuryl dichloride; bromine; sodium methylate; oxalic acid; titanium tetrachloride; sodium hydrogencarbonate; toluene-4-sulfonic acid; silver carbonate; lithium chloride; In diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; pentane;

DOI:10.1021/jo00102a022

upstream raw materials:

1-Isocyanato-2,2-dimethyl-cyclopropanecarboxylic acid methyl ester

1-Ethoxycarbonylamino-2,2-dimethyl-cyclopropanecarboxylic acid methyl ester

3-methyl-butan-2-one

4-hydroxy-3,3-dimethyl-butan-2-one

Refernces

• 1、 Boeykens,De Kimpe,Abbaspour Tehrani. "Synthesis of 1-amino-2,2-dialkylcyclopropanecarboxylic acids via base-induced cyclization of γ-chloro-α-imino ester". . p. 6973 - 6985. Retrieved 2007/10/02.