(2'S,3S)-1-(2-Methylamino-2-Phenyl-Ethyl)-Pyrrolidin-3-Ol

Base Information

• Chemical Name: (2'S,3S)-1-(2-Methylamino-2-Phenyl-Ethyl)-Pyrrolidin-3-Ol
• CAS No.: 142773-73-7
• Molecular Formula: C13H20N2O
• Molecular Weight: 220.315
• DSSTox Substance ID: DTXSID50374905
• Wikidata: Q82163480
• Mol file: 142773-73-7.mol

Synonyms:142773-73-7;(2'S,3S)-1-(2-Methylamino-2-Phenyl-Ethyl)-Pyrrolidin-3-Ol;(S)-1-((S)-2-(methylamino)-2-phenylethyl)pyrrolidin-3-ol;(3S)-1-[(2S)-2-(methylamino)-2-phenylethyl]pyrrolidin-3-ol;(2/'S,3S)-1-(2-METHYLAMINO-2-PHENYL-ETHYL)-PYRROLIDIN-3-OL;SCHEMBL5343323;DTXSID50374905;MFCD03426430;AS-41008;CS-0172417;1-(S-2-Methylamino-2-phenylethyl)-S-3-pyrrolidinol;(2'S,3S)-1-(2-methylamino-2-phenyl-ethyl)-pyrrolidin-3-ol, AldrichCPR

Chemical Property of (2'S,3S)-1-(2-Methylamino-2-Phenyl-Ethyl)-Pyrrolidin-3-Ol

Chemical Property:

• Boiling Point: 353.7oC at 760 mmHg
• Flash Point: 167.7oC
• PSA: 35.50000
• Density: 1.095g/cm3
• LogP: 1.34250
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 220.157563266
• Heavy Atom Count: 16
• Complexity: 204

Purity/Quality:

97% ^*data from raw suppliers

(2''S,3S)-1-(2-Methylamino-2-phenyl-ethyl)-pyrrolidin-3-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNC(CN1CCC(C1)O)C2=CC=CC=C2
• Isomeric SMILES: CN[C@H](CN1CC[C@@H](C1)O)C2=CC=CC=C2
• Uses: (2''S,3s)-1-(2-Methylamino-2-Phenyl-Ethyl)-Pyrrolidin-3-Ol (cas# 142773-73-7) is used as a reagent in the preparation of novel heterobicyclic compounds as kappa opioid receptor agonists.

Technology Process of (2'S,3S)-1-(2-Methylamino-2-Phenyl-Ethyl)-Pyrrolidin-3-Ol

There total 7 articles about (2'S,3S)-1-(2-Methylamino-2-Phenyl-Ethyl)-Pyrrolidin-3-Ol 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: 90.0%

ethyl ((S)-2-((S)-3-hydroxypyrrolidin-1-yl)-2-oxo-1-phenylethyl) (207847-98-1) → N-Methyl-N[(1S)-1-phenyl-2-((3S)-3-hydroxypyrrolidine-1-yl)]ethane (142773-73-7)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 3h; Reflux;

Reference yield: 70.0%

Benzoic acid (S)-1-((S)-2-tert-butoxycarbonylamino-2-phenyl-acetyl)-pyrrolidin-3-yl ester (479687-09-7) → N-Methyl-N[(1S)-1-phenyl-2-((3S)-3-hydroxypyrrolidine-1-yl)]ethane (142773-73-7)

Guidance literature:

With lithium aluminium tetrahydride; In toluene; at 0 - 80 ℃; for 18h;

DOI:10.1039/b204844b

Reference yield:

(2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethanoic acid (2900-27-8) → N-Methyl-N[(1S)-1-phenyl-2-((3S)-3-hydroxypyrrolidine-1-yl)]ethane (142773-73-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / DCC; HOBt / CH₂Cl₂

2: 70 percent / LiAlH₄ / toluene / 18 h / 0 - 80 °C

With lithium aluminium tetrahydride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In dichloromethane; toluene;

DOI:10.1039/b204844b

upstream raw materials:

Benzoic acid (S)-1-((S)-2-tert-butoxycarbonylamino-2-phenyl-acetyl)-pyrrolidin-3-yl ester

(2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethanoic acid

ethyl ((S)-2-((S)-3-hydroxypyrrolidin-1-yl)-2-oxo-1-phenylethyl)

(S)-N-(benzyloxycarbonyl)phenylglycine