(S)-(-)-2-(Diphenylmethyl)pyrrolidine

Base Information

• Chemical Name: (S)-(-)-2-(Diphenylmethyl)pyrrolidine
• CAS No.: 119237-64-8
• Molecular Formula: C₁₇H₁₉N
• Molecular Weight: 237.345
• Hs Code.: 29339900
• European Community (EC) Number: 634-253-9
• UNII: UH7U0MAY6C
• DSSTox Substance ID: DTXSID80922897
• Nikkaji Number: J810.000D
• Wikipedia: 2-Diphenylmethylpyrrolidine
• Wikidata: Q27456141
• Mol file: 119237-64-8.mol

Synonyms:119237-64-8;(S)-2-benzhydrylpyrrolidine;(S)-(-)-2-(Diphenylmethyl)pyrrolidine;(S)-2-DIPHENYLMETHYLPYRROLIDINE;(2S)-2-benzhydrylpyrrolidine;(2S)-2-(diphenylmethyl)pyrrolidine;(2S)-2-Benzylhydrylpyrrolidine;(2~{S})-2-(diphenylmethyl)pyrrolidine;MFCD00799525;Pyrrolidine, 2-(diphenylmethyl)-, (2S)-;(2S)-2-(DIPHENYLMETHYL)PYRROLIDINE HYDROCHLORIDE;UH7U0MAY6C;60H;2alpha-Benzhydrylpyrrolidine;(s)-2-benzhydryl-pyrrolidine;SCHEMBL2844473;DTXSID80922897;AM8911;BBL101601;STL555397;AKOS005259913;AKOS015902012;AC-6130;CS-W012845;FS-5610;2-DIPHENYLMETHYLPYRROLIDINE, (S)-;D3804;(S)-(-)-2-(Diphenylmethyl)pyrrolidine, 97%;N12502;PYRROLIDINE, 2-(DIPHENYLMETHYL)-, (S)-;J-004088;Q27456141;PYRROLIDINE, 2-(DIPHENYLMETHYL)-, (2S)-(-)-

Chemical Property of (S)-(-)-2-(Diphenylmethyl)pyrrolidine

Chemical Property:

• Appearance/Colour: Clear colorless to pale yellow oil
• Vapor Pressure: 4.64E-05mmHg at 25°C
• Refractive Index: n20/D 1.587(lit.)
• Boiling Point: 349.6 °C at 760 mmHg
• PKA: 10.68±0.10(Predicted)
• Flash Point: 170.8 °C
• PSA: 12.03000
• Density: 1.046 g/cm³
• LogP: 3.89930
• Storage Temp.: Refrigerator (+4°C)
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 237.151749610
• Heavy Atom Count: 18
• Complexity: 220

Purity/Quality:

97% ^*data from raw suppliers

(S)-(-)-2-(Diphenylmethyl)pyrrolidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CC(NC1)C(C2=CC=CC=C2)C3=CC=CC=C3
• Isomeric SMILES: C1C[C@H](NC1)C(C2=CC=CC=C2)C3=CC=CC=C3
• Uses: Used as excellent chiral solvating agents to determine the enantiomeric composition of chiral carboxylic acids directly by NMR analysis.

Technology Process of (S)-(-)-2-(Diphenylmethyl)pyrrolidine

There total 10 articles about (S)-(-)-2-(Diphenylmethyl)pyrrolidine 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: 91.0%

(S)-2-Benzhydryl-1-benzyl-pyrrolidine (118971-05-4) → (S)-2-(diphenylmethyl)pyrrolidine (22348-31-8,119237-64-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 3h; Heating;

Reference yield: 86.0%

7,7-diphenyl-4,5,6,6a-tetrahydro-1H,3H-pyrrolo<1,2-c>oxazol-2-one (160424-29-3) → (S)-2-(diphenylmethyl)pyrrolidine (22348-31-8,119237-64-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 48h; Ambient temperature;

DOI:10.1016/S0957-4166(96)00495-8

Reference yield:

(S)-proline-N-ethyl carbamate methyl ester (77581-28-3,93423-88-2) → (S)-2-(diphenylmethyl)pyrrolidine (22348-31-8,119237-64-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / tetrahydrofuran / 3 h / Heating

2: 86 percent / H₂ / Pd/C / methanol / 48 h / Ambient temperature

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol;

DOI:10.1016/S0957-4166(96)00495-8

upstream raw materials:

(S)-2-Benzhydryl-1-benzyl-pyrrolidine

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

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

phenylmagnesium bromide

Downstream raw materials:

(R)-2-((S)-2-benzhydrylpyrrolidin-1-yl)-1-phenylethanamine

(R)-2-amino-1-((S)-2-benzhydrylpyrrolidin-1-yl)-2-phenylethanone

benzyl ((R)-2-((S)-2-benzhydrylpyrrolidin-1-yl)-2-oxo-1-phenylethyl)carbamate

(S)-1-(4-(2-benzhydrylpyrrolidin-1-yl)-4-oxobutyl)pyrimidine-2,4(1H,3H)-dione

Refernces

• 1、 An, Feng,Maji, Biplab,Min, Elizabeth,Ofial, Armin R.,Mayr, Herbert. "Basicities and Nucleophilicities of Pyrrolidines and Imidazolidinones Used as Organocatalysts". supporting information. p. 1526 - 1547. Retrieved 2020/02/04.
• 2、 Fernandez, Rosario,Martin-Zamora, Eloisa,Pareja, Carmen,Vazquez, Juan,Diez, Elena,Monge, Angeles,Lassaletta. "Synthesis of enantiopure α-alkoxy-α-trifluoromethyl aldehydes and carboxylic acids from trifluoromethyl ketones". . p. 3428 - 3430. Retrieved 2007/10/03.