Methyl (2S)-(-)-2-(hydroxydiphenylmethyl)-1-pyrrolidinecarboxylate

Base Information

• Chemical Name: Methyl (2S)-(-)-2-(hydroxydiphenylmethyl)-1-pyrrolidinecarboxylate
• CAS No.: 352535-68-3
• Molecular Formula: C19H21 N O3
• Molecular Weight: 311.381
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID90448578
• Nikkaji Number: J1.821.742B
• Wikidata: Q72491303
• Mol file: 352535-68-3.mol

Synonyms:352535-68-3;Methyl (2S)-(-)-2-(hydroxydiphenylmethyl)-1-pyrrolidinecarboxylate;Methyl (2S)-2-[hydroxy(diphenyl)methyl]pyrrolidine-1-carboxylate;Methyl (2S)-()-2-(hydroxydiphenylmethyl)-1-pyrrolidinecarboxylate;DTXSID90448578;methyl (2S)-2-(hydroxydiphenylmethyl)pyrrolidine-1-carboxylate;methyl (S)-2-(hydroxydiphenylmethyl)pyrrolidine-1-carboxylate;(S)-(-)-N-Carbomethoxy-alpha,alpha-diphenyl-2-pyrrolidinemethanol;Methyl(2S)-(-)-2-(hydroxydiphenylmethyl)-1-pyrrolidinecarboxylate;Methyl (2S)-(-)-2-(hydroxydiphenylmethyl)-1-pyrrolidinecarboxylate, 98%;(2S)-2alpha-(Hydroxydiphenylmethyl)pyrrolidine-1-carboxylic acid methyl ester

Chemical Property of Methyl (2S)-(-)-2-(hydroxydiphenylmethyl)-1-pyrrolidinecarboxylate

Chemical Property:

• Melting Point: 160-164 °C(lit.)
• PSA: 49.77000
• LogP: 3.09120
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 311.15214353
• Heavy Atom Count: 23
• Complexity: 381

Purity/Quality:

99% ^*data from raw suppliers

Methyl (2S)-(?)-2-(hydroxydiphenylmethyl)-1-pyrrolidinecarboxylate 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)N1CCCC1C(C2=CC=CC=C2)(C3=CC=CC=C3)O
• Isomeric SMILES: COC(=O)N1CCC[C@H]1C(C2=CC=CC=C2)(C3=CC=CC=C3)O

Technology Process of Methyl (2S)-(-)-2-(hydroxydiphenylmethyl)-1-pyrrolidinecarboxylate

There total 4 articles about Methyl (2S)-(-)-2-(hydroxydiphenylmethyl)-1-pyrrolidinecarboxylate 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%

(S)-diphenylprolinol (22348-32-9,63401-04-7,112022-88-5,112068-01-6) + methyl chloroformate (79-22-1) → methyl (S)-(-)-2-(hydroxy(diphenyl)methyl)-1-pyrrolidine carboxylate (352535-68-3,160424-38-4,352535-69-4)

Guidance literature:

With triethylamine; In diethyl ether; at 20 ℃;

DOI:10.1021/ol026327h

Reference yield:

phenylmagnesium bromide → methyl (S)-(-)-2-(hydroxy(diphenyl)methyl)-1-pyrrolidine carboxylate (352535-68-3,160424-38-4,352535-69-4)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrahydrofuran / Heating

2: 90 percent / KOH / methanol / 4 h / Heating

3: 90 percent / Et₃N / diethyl ether / 20 °C

With potassium hydroxide; triethylamine; In tetrahydrofuran; methanol; diethyl ether;

DOI:10.1021/ol026327h

Reference yield:

(S)-proline-N-ethyl carbamate methyl ester (77581-28-3,93423-88-2) → methyl (S)-(-)-2-(hydroxy(diphenyl)methyl)-1-pyrrolidine carboxylate (352535-68-3,160424-38-4,352535-69-4)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrahydrofuran / Heating

2: 90 percent / KOH / methanol / 4 h / Heating

3: 90 percent / Et₃N / diethyl ether / 20 °C

With potassium hydroxide; triethylamine; In tetrahydrofuran; methanol; diethyl ether;

DOI:10.1021/ol026327h

upstream raw materials:

(S)-diphenylprolinol

methyl chloroformate

(S)-proline-N-ethyl carbamate methyl ester

ethyl (S)-(-)-2--1-pyrrolidinecarboxylate

Downstream raw materials:

(S)-diphenylprolinol

7,7-diphenyl-4,5,6,6a-tetrahydro-1H,3H-pyrrolo<1,2-c>oxazol-2-one

Refernces