cis-2-Boc-hexahydropyrrolo[3,4-c]pyrrole

Base Information

• Chemical Name: cis-2-Boc-hexahydropyrrolo[3,4-c]pyrrole
• CAS No.: 250275-15-1
• Molecular Formula: C₁₁H₂₀N₂O₂
• Molecular Weight: 212.292
• Hs Code.: 2933990090
• European Community (EC) Number: 689-843-9
• DSSTox Substance ID: DTXSID90363898
• Mol file: 250275-15-1.mol

Synonyms:250275-15-1;cis-2-Boc-hexahydropyrrolo[3,4-c]pyrrole;cis-2-Boc-Hexahydropyrrol[3,4-c]pyrrole;(3aR,6aS)-tert-butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate;tert-butyl (3aR,6aS)-2,3,3a,4,6,6a-hexahydro-1H-pyrrolo[3,4-c]pyrrole-5-carboxylate;MFCD04116224;tert-butyl (3aS,6aR)-2,3,3a,4,6,6a-hexahydro-1H-pyrrolo[3,4-c]pyrrole-5-carboxylate;tert-Butyl cis-hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate;tert-butyl cis-octahydropyrrolo[3,4-c]pyrrole-2-carboxylate;tert-butyl (3aR,6aS)-octahydropyrrolo[3,4-c]pyrrole-2-carboxylate;tert-Butyl (3aR,6aS)-hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate;cis-2-Boc-hexahydro-pyrrolo[3,4-c]pyrrole;SCHEMBL649983;DTXSID90363898;BCP23565;AKOS015900121;AM803580;DS-12463;A5092;EN300-100907;N12274;Z1341480014;3-tert-butoxycarbonyl-cis-3,7-diazabicyclo[3.3.0]octane;tert-butyl cis-hexahydropyrrolo[3,4-c]pyrrole-2-carboxylate;meso-tert-Butyl hexahydropyrrolo-[3,4-c]pyrrole-2(1H)-carboxylate;meso-tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate;cis-hexahydropyrrolo[3,4-c]pyrrole-2-carboxylic acid tert-butyl ester;(3aR,6aS)-Hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic acid tert-butyl ester;(cis-racemic)-tert-Butyl hexahydropyrrolo-[3,4-c]pyrrole-2(1H)-carboxylate95%;meso-tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate, AldrichCPR

Chemical Property of cis-2-Boc-hexahydropyrrolo[3,4-c]pyrrole

Chemical Property:

• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: 1.494
• Boiling Point: 295.397 °C at 760 mmHg
• PKA: 10.72±0.20(Predicted)
• Flash Point: 132.451 °C
• PSA: 41.57000
• Density: 1.076 g/cm³
• LogP: 1.33940
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 212.152477885
• Heavy Atom Count: 15
• Complexity: 248

Purity/Quality:

99%, ^*data from raw suppliers

cis-2-Boc-hexahydropyrrolo[3,4-c]pyrrole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC2CNCC2C1
• Isomeric SMILES: CC(C)(C)OC(=O)N1C[C@H]2CNC[C@H]2C1

Technology Process of cis-2-Boc-hexahydropyrrolo[3,4-c]pyrrole

There total 4 articles about cis-2-Boc-hexahydropyrrolo[3,4-c]pyrrole 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: 88.0%

(3aR,6aS)-tert-butyl 5-benzylhexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (370879-56-4) → tert-butyl (3aR,6aS)-hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (250275-15-1,1256094-14-0)

Guidance literature:

palladium-carbon; In ethanol;

Reference yield:

cis-3-benzyl-3,7-diazabicyclo[3.3.0]octane (172739-04-7) → tert-butyl (3aR,6aS)-hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (250275-15-1,1256094-14-0)

Guidance literature:

Multi-step reaction with 2 steps

1: dichloromethane / 24 h / 23 °C / Inert atmosphere

2: hydrogen; acetic acid; palladium 10% on activated carbon / methanol / 72 h / 3620.13 Torr / Inert atmosphere

With palladium 10% on activated carbon; hydrogen; acetic acid; In methanol; dichloromethane;

DOI:10.1021/acs.jmedchem.5b00742

Reference yield:

(3aR,6aS)-5-benzyltetrahydropyrrolo[3,4-c]pyrrole-1,3(2H,3aH)-dione (370879-53-1) → tert-butyl (3aR,6aS)-hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (250275-15-1,1256094-14-0)

Guidance literature:

Multi-step reaction with 3 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 3.5 h / 0 °C / Inert atmosphere; Reflux

2: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5 h / 20 °C

3: 10 wt% Pd(OH)2 on carbon; hydrogen / methanol / 60 °C / 3102.97 Torr

With lithium aluminium tetrahydride; 10 wt% Pd(OH)2 on carbon; hydrogen; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol;

upstream raw materials:

(3aR,6aS)-tert-butyl 5-benzylhexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate

cis-3-benzyl-3,7-diazabicyclo[3.3.0]octane

di-tert-butyl dicarbonate

(3aR,6aS)-5-benzyltetrahydropyrrolo[3,4-c]pyrrole-1,3(2H,3aH)-dione

Downstream raw materials:

tert-butyl cis-5-(6-phenylpyridazine-3-yl)-hexahydro-pyrrolo[3,4-c]-pyrrole-2(1H)-carboxylate

tert-butyl cis-5-(4-bromophenyl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate

(3aR,6aS)-tert-butyl 5-(6-(2-methylbenzylcarbamoyl)pyrazin-2-yl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate

(3aR,6aS)-tert-butyl 5-(6-(3-isopropoxyphenylcarbamoyl)pyrazin-2-yl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate

Refernces

• 1、 -. "QUINOLONE DERIVATIVES AS FIBROBLAST GROWTH FACTOR RECEPTOR INHIBITORS". Page/Page column 139; 140. . Retrieved 2015/09/23.
• 2、 -. "Selective Ligands for the Neuronal Nicotinic Receptors and Uses Thereof". Page/Page column 10. . Retrieved 2009/12/04.