(1S,4S)-2-BOC-2,5-DIAZABICYCLO[2.2.1]HEPTANE

Base Information

• Chemical Name: (1S,4S)-2-BOC-2,5-DIAZABICYCLO[2.2.1]HEPTANE
• CAS No.: 113451-59-5
• Molecular Formula: C10H18N2O2
• Molecular Weight: 294.372
• Hs Code.: 29335990
• Mol file: 113451-59-5.mol

Synonyms:1,1-Dimethylethyl(S,S)-2,5-diazabicyclo[2.2.1]heptane-5-carboxylate;N-Boc-(1S,4S)-2,5-Diazabicyclo[2.2.1]heptane;tert-Butyl(1S,4S)-(-)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate;tert-Butyl(1S,4S)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate;2,5-Diazabicyclo[2.2.1]heptane-2-carboxylicacid, 1,1-dimethylethyl ester, (1S)-;(1S,4S)-(-)-2-Boc-2,5-diazabicyclo[2.2.1]heptane;(1S,4S)-2,5-Diazabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester;(1S,4S)-N-Boc-2,5-diazabicyclo[2.2.1]heptane;(1S,4S)-tert-Butyl2,5-diazabicyclo[2.2.1]heptane-2-carboxylate;

Chemical Property of (1S,4S)-2-BOC-2,5-DIAZABICYCLO[2.2.1]HEPTANE

Chemical Property:

• Appearance/Colour: White to slightly beige powder
• Vapor Pressure: 0.005mmHg at 25°C
• Melting Point: 74-76 °C(lit.)
• Refractive Index: 1.501
• Boiling Point: 276.372 °C at 760 mmHg
• PKA: 9.74±0.20(Predicted)
• Flash Point: 120.946 °C
• PSA: 41.57000
• Density: 1.105 g/cm³
• LogP: 1.23430
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Sensitive.: Air Sensitive
• Water Solubility.: Insoluble in water.

Purity/Quality:

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

(1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptane ^*data from reagent suppliers

Safty Information:

• Statements: 34
• Safety Statements: 22-24/25-45-36/37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Uses: It is used as an active pharmaceutical intermediate.

Technology Process of (1S,4S)-2-BOC-2,5-DIAZABICYCLO[2.2.1]HEPTANE

There total 16 articles about (1S,4S)-2-BOC-2,5-DIAZABICYCLO[2.2.1]HEPTANE 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: 100.0%

(2S,4R)-2-(azidomethyl)-1-(tert-butoxycarbonyl)-4-<(methylsulfonyl)oxy>pyrrolidine (113451-54-0) → (1S,4S)-2,5-Diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (113451-59-5,174823-32-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol;

DOI:10.1021/jo00242a051

Reference yield: 90.0%

(1S,4S)-5-Benzyl-2-tert-butoxycarbonyl-2,5-diazabicyclo<2.2.1>heptane (132666-68-3) → (1S,4S)-2,5-Diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (113451-59-5,174823-32-6)

Guidance literature:

With palladium hydroxide 10 wt. % on activated carbon; hydrogen; In methanol; under 3102.97 Torr;

DOI:10.1080/14756366.2017.1363197

Reference yield: 80.6%

tert-butyl (2S,4S)-4-amino-2-(hydroxymethyl)pyrrolidin-1-carboxylate (922139-40-0) → (1S,4S)-2,5-Diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (113451-59-5,174823-32-6)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 22 - 25 ℃; for 12h; Inert atmosphere;

upstream raw materials:

(2S,4R)-2-(azidomethyl)-1-(tert-butoxycarbonyl)-4-<(methylsulfonyl)oxy>pyrrolidine

(1S,4S)-5-Benzyl-2-tert-butoxycarbonyl-2,5-diazabicyclo<2.2.1>heptane

L-4-hydroxyproline methyl ester hydrochloride

4R-4-hydroxyproline

Downstream raw materials:

3-[2-[bis(4-fluorophenyl)methoxy]ethyl]-8-(1S,4S)-N-t-Boc-2,5-diazabicyclo[2.2.1]heptane

(1S,4S)-tert-butyl 5-(6-phenylpyridazin-3-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

(1S,4S)-2-(5-(4-methoxyphenoxy)-3-pyridyl)-5-(tert-butoxycarbonyl)-2,5-diazabicyclo[2.2.1]heptane

C₁₇H₂₁IN₂O₃

Refernces

• 1、 Laskar, Sujay,Sánchez-Sánchez, Luis,Flores, Sebastián M.,López-Mu?oz, Hugo,Escobar-Sánchez, María L.,López-Ortiz, Manuel,Hernández-Rodríguez, Marcos,Regla, Ignacio. "Identification of (1S,4S)-2,5-diazabicyclo[2.2.1]heptane-dithiocarbamate-nitrostyrene hybrid as potent antiproliferative and apoptotic inducing agent against cervical cancer cell lines". . p. 621 - 635. Retrieved 2018/02/09.
• 2、 -. "Preparation method for (1S,4S)-2,5-diazabicyclo[2.2.1]heptane or (1S,4S)-2,5-diazabicyclo [2.2.1]octane derivative". . . Retrieved 2017/06/02.