cis-5-AMino-2-Boc-hexahydro-cyclopenta[c]pyrrole

Base Information

• Chemical Name: cis-5-AMino-2-Boc-hexahydro-cyclopenta[c]pyrrole
• CAS No.: 863600-81-1
• Molecular Formula: C12H20N2O2
• Molecular Weight: 226.319
• Mol file: 863600-81-1.mol

Synonyms:cis-5-AMino-2-Boc-hexahydro-cyclopenta[c]pyrrole;endo-5-Amino-cis-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid tert-butyl ester

Chemical Property of cis-5-AMino-2-Boc-hexahydro-cyclopenta[c]pyrrole

Chemical Property:

• PSA: 55.56000
• LogP: 2.22880

Purity/Quality:

95-99% ^*data from raw suppliers

cis-5-Amino-2-boc-hexahydro-cyclopenta[c]pyrrole 97.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of cis-5-AMino-2-Boc-hexahydro-cyclopenta[c]pyrrole

There total 4 articles about cis-5-AMino-2-Boc-hexahydro-cyclopenta[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: 95.0%

tert-butyl (cis-exo)-5-(benzylamino)-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-2-carboxylate (863600-79-7) → tert-butyl (3aS,6aR)-5-amino-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-2-carboxylate (863600-81-1,1031335-28-0)

Guidance literature:

With hydrogen; palladium(II) hydroxide; In methanol; at 20 ℃; under 760.051 Torr;

DOI:10.1016/j.bmcl.2010.01.080

Reference yield:

(3aR,6aS)-tert-butyl 5-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (146231-54-1) → tert-butyl (3aS,6aR)-5-amino-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-2-carboxylate (863600-81-1,1031335-28-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: acetic acid / dichloromethane / 0.5 h / Cooling with ice; Inert atmosphere

1.2: 12 h / Inert atmosphere

2.1: hydrogen; acetic acid / palladium 10% on activated carbon / methanol / 12 h / 20 - 30 °C

2.2: 20 - 30 °C

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

Reference yield:

N-(tert-butoxycarbonyl)-N-allyl-3-amino-1-propyne (147528-20-9) → tert-butyl (3aS,6aR)-5-amino-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-2-carboxylate (863600-81-1,1031335-28-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: water; dicobalt octacarbonyl / dichloromethane / 3 h / Reflux

2.1: acetic acid / dichloromethane / 0.5 h / Cooling with ice

2.2: 12 h

3.1: hydrogen; acetic acid / palladium 10% on activated carbon / methanol / 12 h

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

upstream raw materials:

tert-butyl (cis-exo)-5-(benzylamino)-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-2-carboxylate

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

N-(tert-butoxycarbonyl)-N-allyl-3-amino-1-propyne

allylpropargylamine

Downstream raw materials:

tert-butyl (cis-exo)-5-benzyloxycarbonylamino-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-2-carboxylate

benzyl (cis-exo)-N-[1,2,3,3a,4,5,6,6a-octahydrocyclopenta[c]pyrrol-5-yl]carbamate

benzyl (cis-exo)-N-[2-methyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-5-yl]carbamate

Refernces

• 1、 -. "DIHYDROPTERIDINONE DERIVATIVES, PREPARATION PROCESS AND PHARMACEUTICAL USE THEREOF". Page/Page column 34. . Retrieved 2012/07/28.
• 2、 Lowe III, John A.,DeNinno, Shari L.,Drozda, Susan E.,Schmidt, Christopher J.,Ward, Karen M.,David Tingley III,Sanner, Mark,Tunucci, Don,Valentine, James. "An octahydro-cyclopenta[c]pyrrole series of inhibitors of the type 1 glycine transporter". supporting information; experimental part. p. 907 - 911. Retrieved 2010/08/19.