methyl 1,6-diazabicyclo[3.1.0]hexane-5-carboxylate

Base Information

• Chemical Name: methyl 1,6-diazabicyclo[3.1.0]hexane-5-carboxylate
• CAS No.: 89019-22-7
• Molecular Formula: C6H10N2O2
• Molecular Weight: 142.1558
• Mol file: 89019-22-7.mol

Synonyms:Methyl 1,6-diazabicyclo[3.1.0]hexane-5-carboxylate;5-methoxycarbonyl-1,6-diaza-bicyclo(3.1.0)hexane;1,6-diazabicyclo[3.1.0]hexane-5-carboxylic acid methyl ester;5-Carbomethoxy-1,6-diazabicyclo<3.1.0>hexane;

Chemical Property of methyl 1,6-diazabicyclo[3.1.0]hexane-5-carboxylate

Chemical Property:

• Vapor Pressure: 1.3mmHg at 25°C
• Boiling Point: 172.9°Cat760mmHg
• PKA: 4.11±0.40(Predicted)
• Flash Point: 58.4°C
• PSA: 51.25000
• Density: 1.3g/cm³
• LogP: -0.26360

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of methyl 1,6-diazabicyclo[3.1.0]hexane-5-carboxylate

There total 1 articles about methyl 1,6-diazabicyclo[3.1.0]hexane-5-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: 50.0%

methyl-Δ1-pyrroline-2-carboxylate (57224-14-3) → 1,6-diazabicyclo<3.1.0>hexane-5-carboxylic acid methyl ester (89019-22-7,111265-47-5,111265-50-0,111265-53-3)

Guidance literature:

With NCI-88947; N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate; hydroxylamine-O-sulfonic acid; In benzene; at 20 ℃; for 10h;

DOI:10.1007/BF00954608

Reference yield: 97.0%

1,6-diazabicyclo<3.1.0>hexane-5-carboxylic acid methyl ester (89019-22-7,111265-47-5,111265-50-0,111265-53-3) + methylamine (74-89-5) → 5-N-Methylcarbomoyl-1,6-diazabicyclo<3.1.0>hexane (89019-23-8,111265-51-1)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 72h;

DOI:10.1007/BF00954608

Reference yield:

1,6-diazabicyclo<3.1.0>hexane-5-carboxylic acid methyl ester (89019-22-7,111265-47-5,111265-50-0,111265-53-3) → endo-5-N-Methylcarbomoyl-6-chloro-1,6-diazabicyclo<3.1.0>hexane (89019-25-0,108392-48-9,108392-50-3,113085-29-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / MeONa / methanol / 20 °C

2: t-BuOCl / CH₂Cl₂ / -30 °C

With tert-butylhypochlorite; sodium methylate; In methanol; dichloromethane;

DOI:10.1039/c39830001275

upstream raw materials:

methyl-Δ¹-pyrroline-2-carboxylate

Downstream raw materials:

5-N-Methylcarbomoyl-1,6-diazabicyclo<3.1.0>hexane

endo-5-N-Methylcarbomoyl-6-chloro-1,6-diazabicyclo<3.1.0>hexane

methylamide of (1S,5S,6S)-1,6-diazabicyclo<3.1.0>hexane-5-carboxylic acid