Methyl 1-benzylazetidine-2-carboxylate

Base Information

• Chemical Name: Methyl 1-benzylazetidine-2-carboxylate
• CAS No.: 18085-37-5
• Molecular Formula: C12H15NO2
• Molecular Weight: 205.257
• Hs Code.: 2933990090
• European Community (EC) Number: 858-947-8
• DSSTox Substance ID: DTXSID20402709
• Nikkaji Number: J2.196.422K
• Mol file: 18085-37-5.mol

Synonyms:Methyl 1-benzylazetidine-2-carboxylate;18085-37-5;2-Azetidinecarboxylic acid, 1-(phenylmethyl)-, methyl ester;1-BENZYL-AZETIDINE-2-CARBOXYLIC ACID METHYL ESTER;117396-78-8;MFCD06657098;EICOSAPENTAENOIC ACID [5,6,8 9,11,12,14,15,17,18-3 H];Methyl1-benzylazetidine-2-carboxylate;1-BENZYL-2-(METHOXYCARBONYL)AZETIDINE;SCHEMBL2768950;DTXSID20402709;CTFFWKWHYDAMKP-UHFFFAOYSA-N;CFA38220;AB1510;AKOS004115371;AKOS016344668;methyl N-benzylazetidine-2-carboxylate;AC-2631;DS-2187;Methyl-1-benzylazetidine-2-carboxylate;PB14455;SB15488;SB15489;AM808144;SY002344;BB 0262990;CS-0042582;FT-0693505;FT-0771786;FT-0772281;A22740;EN300-133259;1-Benzylazetidine-2-carboxylic acid methyl ester;N-Benzylazetidine-2-carboxylic acid methyl ester;J-521749

Chemical Property of Methyl 1-benzylazetidine-2-carboxylate

Chemical Property:

• Vapor Pressure: 0.00596mmHg at 25°C
• Refractive Index: 1.559
• Boiling Point: 272.8 °C at 760 mmHg
• PKA: 6.42±0.40(Predicted)
• Flash Point: 100.6 °C
• PSA: 29.54000
• Density: 1.153 g/cm³
• LogP: 1.37180
• Storage Temp.: 2-8°C
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 205.110278721
• Heavy Atom Count: 15
• Complexity: 224

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methyl1-Benzylazetidine-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CCN1CC2=CC=CC=C2

Technology Process of Methyl 1-benzylazetidine-2-carboxylate

There total 4 articles about Methyl 1-benzylazetidine-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: 67.0%

methyl 2,4-dibromobutanoate (29547-04-4,70288-65-2) + benzylamine (100-46-9) → methyl 1-benzyl-2-azetidinecarboxylate (18085-37-5)

Guidance literature:

With triethylamine; In acetonitrile; for 4h; Reflux;

DOI:10.1016/j.tet.2012.03.111

Reference yield: 45.0%

pentacarbonyl(N-benzyl-2-azacyclobutylidene)chromium(0) (124685-61-6) → benzyl(3,3-dimethoxypropyl)amine (124619-68-7) + methyl 1-benzyl-2-azetidinecarboxylate (18085-37-5) + chromium(0) hexacarbonyl (199620-14-9,13007-92-6)

Guidance literature:

With methanol; In methanol; Irradiation (UV/VIS); solid carbene complex in dry methanol is added to an oven-dried Pyrex pressure tube, contents are degassed, purged with Ar, warmed to room temp., purged with CO, pressurized with 50-90 psi CO, irradiated (450 W) for 8 d; monitored by TLC, mixt. is filtered (Celite) to remove solid Cr(CO)6, evapn. in vacuo yields mixt. of two compds., sepn. by chromy. (CH3OH/CH2Cl2); NMR, IR, elem. anal.;

Reference yield: 45.0%

methanol (67-56-1) + carbon monoxide (201230-82-2) → benzyl(3,3-dimethoxypropyl)amine (124619-68-7) + methyl 1-benzyl-2-azetidinecarboxylate (18085-37-5)

Guidance literature:

for 192h; under 2585.7 - 4654.3 Torr; Ambient temperature; Irradiation;

upstream raw materials:

methyl 2,4-dibromobutanoate

benzylamine

methanol

carbon monoxide

Downstream raw materials:

1-benzylazetidine-2-carboxamide

(S)-(-)-1-benzylazetidine-2-carboxamide

(R)-(+)-methyl 1-benzylazetidine-2-carboxylate

1-benzylpyrrolidine-2,2,3-tricarboxylic acid 3-methyl 2,2-diethyl ester

Refernces

• 1、 Nocquet, Pierre-Antoine,Hazelard, Damien,Compain, Philippe. "Synthesis of spirocyclopropyl γ-lactams by tandem intramolecular azetidine ring-opening/closing cascade reaction: Synthetic and mechanistic aspects". experimental part. p. 4117 - 4128. Retrieved 2012/07/28.
• 2、 -. "Process". . . Retrieved 2008/06/13.