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

Base Information

• Chemical Name: 5-Hydroxymethyl-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid tert-butyl ester
• CAS No.: 650578-12-4
• Molecular Formula: C13H21NO3
• Molecular Weight: 241.331
• Hs Code.: 2933990090
• Mol file: 650578-12-4.mol

Synonyms:5-Hydroxymethyl-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid tert-butyl ester;Cyclopenta[c]pyrrole-2(1H...;Cyclopenta[c]pyrrole-2(1H)-carboxylic acid, hexahydro-5-(hydroxyMethyl)-, 1,1-diMethylethyl ester;5-Hydroxymethyl-2-BOC-hexahydrocyclopenta[C]pyrrole;tert-butyl 5-(hydroxymethyl)-octahydrocyclopenta[c]pyrrole-2-carboxylate

Chemical Property of 5-Hydroxymethyl-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid tert-butyl ester

Chemical Property:

• PSA: 49.77000
• LogP: 1.80970

Purity/Quality:

99% ^*data from raw suppliers

Hexahydro-5-(hydroxymethyl)cyclopenta[c]pyrrole-2(1H)-carboxylic acid, 1,1-dimethylethyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-Hydroxymethyl-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid tert-butyl ester

There total 5 articles about 5-Hydroxymethyl-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: 84.0%

(3aR,5s,6aS)-tert-butyl 5-formylhexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate → tert-butyl (3aR,6aS)-5-(hydroxymethyl)-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole2-carboxylate (650578-12-4)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 25 ℃; for 0.166667h;

Reference yield:

tert-butyl (3aR,6aS)-5-methylene-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrole-2-carboxylate (139228-12-9) → tert-butyl (3aR,6aS)-5-(hydroxymethyl)-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole2-carboxylate (650578-12-4) + tert-butyl (3aR,6aS)-5-(hydroxymethyl)-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole2-carboxylate

Guidance literature:

tert-butyl (3aR,6aS)-5-methylene-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrole-2-carboxylate; With 2,3-Dimethyl-2-butene; dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 20 ℃; for 19h; Inert atmosphere;

With dihydrogen peroxide; sodium hydroxide; In tetrahydrofuran; water; at 0 - 20 ℃; for 2h;

Reference yield:

tert-butyl 5-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (148404-28-8) → tert-butyl (3aR,6aS)-5-(hydroxymethyl)-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole2-carboxylate (650578-12-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium tert-butylate / tetrahydrofuran / 12 h / 0 - 25 °C

2.1: hydrogenchloride / tetrahydrofuran / 2 h / 100 °C

2.2: 1 h / 25 °C

3.1: sodium tetrahydroborate / methanol / 0.17 h / 25 °C

With hydrogenchloride; sodium tetrahydroborate; potassium tert-butylate; In tetrahydrofuran; methanol;

upstream raw materials:

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

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

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

Downstream raw materials:

(5Z)-5-({(3aR,5r,6aS)-2-[2,4-bis(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-5-yl}methylidene)-4-(prop-2-yn-1-ylamino)-1,3-thiazol-2(5H)-one

(3aR,6aS)-2-[2,4-bis(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrole-5-carbaldehyde

{(3aR,6aS)-2-[2,4-bis(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-5-yl}methanol

(5Z)-5-({(3aR,5r,6aS)-2-[2,4-bis(trifluoromethyl)phenyl]octahydrocyclopenta[c]pyrrol-5-yl}methylidene)-4-(prop-2-yn-1-ylamino)-1,3-thiazol-2(5H)-one

Refernces

• 1、 -. "ANTAGONISTS OF THE MUSCARINIC ACETYLCHOLINE RECEPTOR M4". . . Retrieved 2019/05/10.