(2S,3aS,6aS)-1-(tert-butoxycarbonyl)octahydrocyclopenta[b]pyrrole-2-carboxylic acid

Base Information

• Chemical Name: (2S,3aS,6aS)-1-(tert-butoxycarbonyl)octahydrocyclopenta[b]pyrrole-2-carboxylic acid
• CAS No.: 124002-32-0
• Molecular Formula: C13H21NO4
• Molecular Weight: 255.314
• European Community (EC) Number: 845-557-8
• Mol file: 124002-32-0.mol

Synonyms:124002-32-0;(2S,3aS,6aS)-1-(tert-butoxycarbonyl)octahydrocyclopenta[b]pyrrole-2-carboxylic acid;(2S,3aS,6aS)-1-[(2-methylpropan-2-yl)oxycarbonyl]-3,3a,4,5,6,6a-hexahydro-2H-cyclopenta[b]pyrrole-2-carboxylic acid;(2S,3aS,6aS)-1-[(tert-butoxy)carbonyl]-octahydrocyclopenta[b]pyrrole-2-carboxylate;(2S,3aS,6aS)-1-[(tert-butoxy)carbonyl]-octahydrocyclopenta[b]pyrrole-2-carboxylic acid;Cyclopenta[b]pyrrole-1,2(2H)-dicarboxylic acid, hexahydro-, 1-(1,1-dimethylethyl) ester, (2S,3aS,6aS)-;SCHEMBL241194;MHOIOLLMOIIRTR-GUBZILKMSA-N;AKOS027322154;(2S,3aS,6aS)-1-tert-butoxycarbonyl-3,3a,4,5,6,6a-hexahydro-2H-cyclopenta[b]pyrrole-2-carboxylic acid;AS-74783;CS-0127846;W14483;EN300-1071335;(2S,3aS,6aS)-1-(tert-butoxycarbonyl)octahydrocyclopenta[b]pyrrole-2-carboxylicacid;(2S,3aS,6aS)-1-Boc-3,3a,4,5,6,6a-hexahydro-2H-cyclopenta[b]pyrrole-2-carboxylic Acid;N-tert.-Butoxycarbonyl-(2S,3aS,6aS)-octahydrocyclopenta[b]pyrrole-2-carboxylic acid

Chemical Property of (2S,3aS,6aS)-1-(tert-butoxycarbonyl)octahydrocyclopenta[b]pyrrole-2-carboxylic acid

Chemical Property:

• Boiling Point: 386.0±25.0 °C(Predicted)
• PKA: 4.03±0.20(Predicted)
• PSA: 66.84000
• Density: 1.196±0.06 g/cm3(Predicted)
• LogP: 2.18700
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 255.14705815
• Heavy Atom Count: 18
• Complexity: 361

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1C2CCCC2CC1C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N1[C@H]2CCC[C@H]2C[C@H]1C(=O)O

Technology Process of (2S,3aS,6aS)-1-(tert-butoxycarbonyl)octahydrocyclopenta[b]pyrrole-2-carboxylic acid

There total 10 articles about (2S,3aS,6aS)-1-(tert-butoxycarbonyl)octahydrocyclopenta[b]pyrrole-2-carboxylic acid 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,3aS,6aS)-2-benzyl 1-tert-butyl hexahydrocyclopenta[b]pyrrole-1,2(2H)-dicarboxylate (124002-38-6) → (2S,3aS,6aS)-1-[(tert-butoxy)carbonyl]octahydrocyclopenta[b]pyrrole-2-carboxylic acid (124002-32-0)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 30 ℃; for 6h; under 45004.5 Torr;

DOI:10.1002/anie.201204594

Reference yield:

benzyl (2S,3AS,6AS)-octahydrocyclopenta[b]pyrrole-2-carboxylate hydrochloride (87269-87-2,87679-25-2,88547-79-9,93779-29-4,94569-19-4,138877-09-5) → (2S,3aS,6aS)-1-[(tert-butoxy)carbonyl]octahydrocyclopenta[b]pyrrole-2-carboxylic acid (124002-32-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dmap; triethylamine / dichloromethane / 0.33 h / 0 °C

1.2: 12 h / 0 - 30 °C

2.1: palladium 10% on activated carbon; hydrogen / methanol / 6 h / 30 °C / 45004.5 Torr

With dmap; palladium 10% on activated carbon; hydrogen; triethylamine; In methanol; dichloromethane;

DOI:10.1002/anie.201204594

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + benzyl (2S,3AS,6AS)-octahydrocyclopenta[b]pyrrole-2-carboxylate hydrochloride (87269-87-2,87679-25-2,88547-79-9,93779-29-4,94569-19-4,138877-09-5) → (2S,3aS,6aS)-1-[(tert-butoxy)carbonyl]octahydrocyclopenta[b]pyrrole-2-carboxylic acid (124002-32-0)

Guidance literature:

Multi-step reaction with 2 steps

1: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 16 h

2: palladium 10% on activated carbon; hydrogen / ethanol / 24 h / 20 °C / 760.05 Torr

With dmap; palladium 10% on activated carbon; hydrogen; N-ethyl-N,N-diisopropylamine; In ethanol; dichloromethane;

upstream raw materials:

di-tert-butyl dicarbonate

(S,S,S)-2-azabicyclo<3.3.0>octane-3-carboxylic acid hydrochloride

(2S,3aS,6aS)-2-benzyl 1-tert-butyl hexahydrocyclopenta[b]pyrrole-1,2(2H)-dicarboxylate

benzyl (2S,3AS,6AS)-octahydrocyclopenta[b]pyrrole-2-carboxylate hydrochloride

Downstream raw materials:

(S)-3-{(2S,4R)-2-[(2S,3aS,6aS)-2-(Benzyl-methyl-carbamoyl)-hexahydro-cyclopenta[b]pyrrole-1-carbonyl]-4-hydroxy-pyrrolidine-1-carbonyl}-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

(S)-2-{(2S,4R)-2-[(2S,3aS,6aS)-2-(Benzyl-methyl-carbamoyl)-hexahydro-cyclopenta[b]pyrrole-1-carbonyl]-4-hydroxy-pyrrolidine-1-carbonyl}-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester