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

Base Information

• Chemical Name: tert-butyl (cis-exo)-5-(benzylamino)-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-2-carboxylate
• CAS No.: 863600-79-7
• Molecular Formula: C₁₉H₂₈N₂O₂
• Molecular Weight: 316.444
• Mol file: 863600-79-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about tert-butyl (cis-exo)-5-(benzylamino)-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-2-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: 100.0%

(3aR,6aS)-tert-butyl 5-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (146231-54-1) + benzylamine (100-46-9) → tert-butyl (cis-exo)-5-(benzylamino)-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-2-carboxylate (863600-79-7)

Guidance literature:

(3aR,6aS)-tert-butyl 5-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate; benzylamine; With acetic acid; In dichloromethane; for 0.5h; Cooling with ice; Inert atmosphere;

With sodium tris(acetoxy)borohydride; In dichloromethane; for 12h; Inert atmosphere;

With sodium hydrogencarbonate; In dichloromethane; water;

Reference yield: 91.0%

(3aR,6aS)-benzyl 5-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (1217315-21-3,148404-29-9) + benzylamine (100-46-9) → tert-butyl (cis-exo)-5-(benzylamino)-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-2-carboxylate (863600-79-7)

Guidance literature:

With sodium tris(acetoxy)borohydride; acetic acid; In 1,2-dichloro-ethane; at 20 ℃; for 16h;

DOI:10.1016/j.bmcl.2009.12.071

Reference yield: 43.0%

tert-butyl (3aR,5r,6aS)-5-hydroxy-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-2-carboxylate (912563-45-2) + benzylamine (100-46-9) → tert-butyl (cis-exo)-5-(benzylamino)-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-2-carboxylate (863600-79-7) + tert-butyl (3aR,5s,6aS)-5-(benzylamino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate

Guidance literature:

With sodium tris(acetoxy)borohydride; In dichloromethane; at 20 ℃; optical yield given as %de;

DOI:10.1016/j.bmcl.2010.01.080

upstream raw materials:

tert-butyl 5-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate

benzylamine

tert-butyl (3aR,5r,6aS)-5-hydroxy-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-2-carboxylate

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

Downstream raw materials:

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

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