tert-butyl 6-oxo-3-aza-bicyclo[3.2.0]heptane-3-carboxylate

Base Information

• Chemical Name: tert-butyl 6-oxo-3-aza-bicyclo[3.2.0]heptane-3-carboxylate
• CAS No.: 663172-80-3
• Molecular Formula: C₁₁H₁₇NO₃
• Molecular Weight: 211.261
• Hs Code.: 2933990090
• Mol file: 663172-80-3.mol

Synonyms:tert-butyl 6-oxo-3-azabicyclo[3.2.0]heptane-3-carboxylate;3-BOC-6-OXO-3-AZABICYCLO[3.2.0]HEPTANE;TERT-BUTYL 6-OXO-3-AZA-BICYCLO[3.2.0]HEPTANE-3-CARBOXYLATE;CIS-6-OXO-3-AZA-BICYCLO[3.2.0]HEPTANE-3-CARBOXYLIC ACID TERT-BUTYL ESTER;

Chemical Property of tert-butyl 6-oxo-3-aza-bicyclo[3.2.0]heptane-3-carboxylate

Chemical Property:

• Appearance/Colour: powder
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.515
• Boiling Point: 308.244oC at 760 mmHg
• Flash Point: 140.221oC
• PSA: 46.61000
• Density: 1.174g/cm3
• LogP: 1.38020
• Storage Temp.: 2-8°C

Purity/Quality:

98%min ^*data from raw suppliers

tert-Butyl6-Oxo-3-azabicyclo[3.2.0]heptane-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of tert-butyl 6-oxo-3-aza-bicyclo[3.2.0]heptane-3-carboxylate

There total 4 articles about tert-butyl 6-oxo-3-aza-bicyclo[3.2.0]heptane-3-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: 79.0%

(cis)-tert-butyl 6-hydroxy-3-azabicyclo[3.2.0]heptane-3-carboxylate (663172-78-9) → tert-butyl 6-oxo-3-azabicyclo[3.2.0]heptane-3-carboxylate (663172-80-3)

Guidance literature:

(cis)-tert-butyl 6-hydroxy-3-azabicyclo[3.2.0]heptane-3-carboxylate; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 0.5h;

With triethylamine; In dichloromethane; at -78 - 40 ℃; for 7h;

Reference yield: 68.0%

di-tert-butyl dicarbonate (24424-99-5) + 3-azabicyclo[3.2.0]heptan-6-ol → tert-butyl 6-oxo-3-azabicyclo[3.2.0]heptane-3-carboxylate (663172-80-3)

Guidance literature:

di-tert-butyl dicarbonate; 3-azabicyclo[3.2.0]heptan-6-ol; With dmap; triethylamine; In dichloromethane; for 12h;

With Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃; for 16h;

DOI:10.1021/acs.joc.8b00077

Reference yield:

C13H17NO → tert-butyl 6-oxo-3-azabicyclo[3.2.0]heptane-3-carboxylate (663172-80-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: palladium 10% on activated carbon; hydrogen / methanol / 12 h / 40 °C / 45603.1 Torr

2.1: dmap; triethylamine / dichloromethane / 12 h

2.2: 16 h / 0 - 20 °C

With dmap; palladium 10% on activated carbon; hydrogen; triethylamine; In methanol; dichloromethane;

DOI:10.1021/acs.joc.8b00077

upstream raw materials:

(cis)-tert-butyl 6-hydroxy-3-azabicyclo[3.2.0]heptane-3-carboxylate

di-tert-butyl dicarbonate

Downstream raw materials:

tert-butyl 6-hydroxy-3-azabicyclo[3.2.0]heptane-3-carboxylate

Refernces

• 1、 -. "Azabicyclic compounds are central nervous system active agents". Page 82. . Retrieved 2010/02/05.