3,6-Diazabicyclo[3.1.1]heptane-6-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 3,6-Diazabicyclo[3.1.1]heptane-6-carboxylic acid tert-butyl ester
• CAS No.: 869494-16-6
• Molecular Formula: C10H18N2O2
• Molecular Weight: 198.265
• Hs Code.: 2933990090
• Mol file: 869494-16-6.mol

Synonyms:3,6-Diazabicyclo[3.1.1]heptane-6-carboxylic acid tert-butyl ester;6-(tert-Butyloxycarbonyl)-3,6-diazabicyclo[3.1.1]heptane;tert-Butyl 3,6-diazabicyclo[3.1.1]heptane-6-carboxylate;(1R,5S)-tert-butyl 3,6-diazabicyclo[3.1.1]heptane-6-carboxylate;3,6-Diazabicyclo[3.1.1]heptane-6-carboxylic acid, 1,1-dimethylethyl ester

Chemical Property of 3,6-Diazabicyclo[3.1.1]heptane-6-carboxylic acid tert-butyl ester

Chemical Property:

• Boiling Point: 276℃
• PKA: 9.53±0.20(Predicted)
• Flash Point: 121℃
• PSA: 41.57000
• Density: 1.104
• LogP: 1.23430
• Storage Temp.: 2-8°C(protect from light)

Purity/Quality:

98%, ^*data from raw suppliers

6-Boc-3,6-diazabicyclo[3.1.1]heptane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Use Description: 3,6-Diazabicyclo[3.1.1]heptane-6-carboxylic acid tert-butyl ester, a specific chemical compound, serves distinct purposes across various fields. In the pharmaceutical sector, it can serve as a building block or intermediate in the synthesis of potential therapeutic compounds, contributing to drug discovery and development. In organic chemistry, this compound plays a crucial role as a reagent or catalyst, facilitating various chemical reactions and enabling the creation of complex molecular structures for research and practical applications. Additionally, in the field of materials science, it may find use in the development of specialized materials due to its unique structural properties. Its applications in pharmaceuticals, chemistry, and materials science highlight its significance in driving innovation, scientific exploration, and practical solutions across these diverse domains.

Technology Process of 3,6-Diazabicyclo[3.1.1]heptane-6-carboxylic acid tert-butyl ester

There total 18 articles about 3,6-Diazabicyclo[3.1.1]heptane-6-carboxylic acid tert-butyl 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: 87.0%

3-benzyl-6-t-butoxycarbonyl-3,6-diazabicyclo[3.1.1]heptane → 3,6-diazabicyclo[3.1.1]heptane-6-carboxylic acid tert-butyl ester (869494-16-6)

Guidance literature:

With hydrogen; palladium 10% on activated carbon; In ethanol; at 60 ℃; for 7h; under 2327.23 Torr;

Reference yield: 81.0%

tert-butyl 3-[(2-nitrophenyl)sulfonyl]-3,6-diazabicyclo[3.1.1]heptane-6-carboxylate (1414540-41-2) → 3,6-diazabicyclo[3.1.1]heptane-6-carboxylic acid tert-butyl ester (869494-16-6)

Guidance literature:

With lithium hydroxide monohydrate; 1-dodecylthiol; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1016/j.tetlet.2012.08.156

Reference yield:

3-benzyl-3,6-diazabicyclo[3.1.1]heptan-2-one (869494-13-3) → 3,6-diazabicyclo[3.1.1]heptane-6-carboxylic acid tert-butyl ester (869494-16-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Heating / reflux

1.2: 0 °C

2.1: tetrahydrofuran / 12.17 h / 0 - 20 °C

3.1: hydrogen / palladium 10% on activated carbon / ethanol / 7 h / 60 °C / 2327.23 Torr

With lithium aluminium tetrahydride; hydrogen; palladium 10% on activated carbon; In tetrahydrofuran; ethanol;

upstream raw materials:

2,4-diethyl (2R,4S)-1-benzylazetidine-2,4-dicarboxylate

1-tert-butyl 2,4-diethyl cis-azetidine-1,2,4-tricarboxylate

2,4-dibromoglutaric acid diethyl ester

tert-butyl (2R,4S)-2,4-bis(hydroxymethyl)azetidine-1-carboxylate

Refernces

• 1、 -. "3,6-DIAZABICYCLOS[3.1.1]HEPTANE DERIVATIVES WITH ANALGESIC ACTIVITY". Page/Page column 11; 19. . Retrieved 2010/02/14.