(3aS,4S,6aR)-5-Methylene-4-(toluene-4-sulfonylamino)-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (3aS,4S,6aR)-5-Methylene-4-(toluene-4-sulfonylamino)-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid tert-butyl ester
• CAS No.: 139228-13-0
• Molecular Formula: C₂₀H₂₈N₂O₄S
• Molecular Weight: 392.519
• Mol file: 139228-13-0.mol

Synonyms:

Chemical Property of (3aS,4S,6aR)-5-Methylene-4-(toluene-4-sulfonylamino)-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,4S,6aR)-5-Methylene-4-(toluene-4-sulfonylamino)-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid tert-butyl ester

There total 2 articles about (3aS,4S,6aR)-5-Methylene-4-(toluene-4-sulfonylamino)-hexahydro-cyclopenta[c]pyrrole-2-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: 82.0%

tert-butyl (3aR,6aS)-5-methylene-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrole-2-carboxylate (139228-12-9) + bis(p-toluenesulfonyl) sulfur diimide (851-06-9) → (3aS,4S,6aR)-5-Methylene-4-(toluene-4-sulfonylamino)-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid tert-butyl ester (139228-13-0,147600-75-7)

Guidance literature:

With potassium carbonate; a) CH₂Cl₂, 0 deg C to r.t.;

DOI:10.1016/S0040-4039(00)60166-1

Reference yield:

5-Methylene-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid tert-butyl ester (151585-62-5) + bis(p-toluenesulfonyl) sulfur diimide (851-06-9) → (3aS,4S,6aR)-5-Methylene-4-(toluene-4-sulfonylamino)-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid tert-butyl ester (139228-13-0,147600-75-7)

Guidance literature:

With potassium carbonate; Yield given. Multistep reaction; 1) CH₂Cl₂, a) 0 deg C, 1 h, b) room temperature, 16 h, 2) H₂O, MeOH, 5 h;

DOI:10.1016/S0040-4020(01)81870-6

Reference yield:

(3aS,4S,6aR)-5-Methylene-4-(toluene-4-sulfonylamino)-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid tert-butyl ester (139228-13-0,147600-75-7) → N-(3S,4R,5R,7R)-1-Aza-tricyclo[3.3.1.03,7]non-4-yl-4-methyl-benzenesulfonamide (139255-61-1,147600-77-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) thexylborane, 2) aq. H₂O₂ / 1) THF

2: oxidation, epimerization, reduction sequence

3: 99 percent / pyridine

4: TFA

5: iPr₂NEt / acetonitrile

With pyridine; thexylborane; dihydrogen peroxide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In acetonitrile;

DOI:10.1016/S0040-4039(00)60166-1

upstream raw materials:

5-Methylene-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid tert-butyl ester

bis(p-toluenesulfonyl) sulfur diimide

tert-butyl (3aR,6aS)-5-methylene-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrole-2-carboxylate

Downstream raw materials:

(3aS,4S,5R,6aR)-5-Hydroxymethyl-4-(toluene-4-sulfonylamino)-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid tert-butyl ester

(3aS,4S,5S,6aR)-5-Hydroxymethyl-4-(toluene-4-sulfonylamino)-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid tert-butyl ester

(+/-)-2,5β-methano-1H-3aα,6aα-cyclopenta[c]pyrrol-4α-amine

N-(3S,4R,5R,7R)-1-Aza-tricyclo[3.3.1.0^3,7]non-4-yl-4-methyl-benzenesulfonamide