(S)-2-(Bis(3,5-bis(trifluoromethyl)phenyl)((trimethylsilyl)oxy)methyl)pyrrolidine

Base Information

• Chemical Name: (S)-2-(Bis(3,5-bis(trifluoromethyl)phenyl)((trimethylsilyl)oxy)methyl)pyrrolidine
• CAS No.: 848821-61-4
• Molecular Formula: C24H23 F12 N O Si
• Molecular Weight: 597.519
• European Community (EC) Number: 628-093-9
• DSSTox Substance ID: DTXSID10461123
• Nikkaji Number: J2.148.498I
• Wikidata: Q76416916
• Mol file: 848821-61-4.mol

Synonyms:848821-61-4;(S)-2-(Bis(3,5-bis(trifluoromethyl)phenyl)((trimethylsilyl)oxy)methyl)pyrrolidine;[bis[3,5-bis(trifluoromethyl)phenyl]-[(2S)-pyrrolidin-2-yl]methoxy]-trimethylsilane;(S)-2-[(Bis(3,5-bis(trifluoromethyl)phenyl)trimethylsilyloxy)methyl]pyrrolidine;(S)-a,a-Bis[3,5-bis(trifluoromethyl)phenyl]-2-pyrrolidinemethanol trimethylsilyl ether;(2S)-2-{Bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilyl)oxy]methyl}pyrrolidine;(S)-2-(BIS(3,5-BIS(TRIFLUOROMETHYL)PHENYL)-((TRIMETHYLSILYL)OXY)METHYL)PYRROLIDINE;(S)-ALPHA,ALPHA-BIS(3,5-BIS(TRIFLUOROMET;SCHEMBL1262080;DTXSID10461123;MOHRGTBNEJKFMB-IBGZPJMESA-N;(S)-ALPHA,ALPHA-BIS(3,5-BIS(TRIFLUOROMETHYL)PHENYL)-2-PYRROLIDINEMETHANOL TRIMETHYLSILYL ETHER;MFCD09750447;AKOS016004078;(S)-|A,|A-Bis[3,5-bis(trifluoromethyl)phenyl]-2-pyrrolidinemethanol trimethylsilyl ether;AS-42927;CS-0091861;A863938;(S)-,-Bis[3,5-bis(trifluoromethyl)phenyl]-2-pyrrolidinemethanol trimethylsilyl ether;(S)-a,a-Bis[3,5-di(trifluoromethyl)phenyl]-O-(trimethylsilyl)pyrrolidine-2-methanol (>85%);(S)-alpha,alpha-Bis[3,5-bis(trifluoromethyl)phenyl]-2-pyrrolidinemethanol trimethylsilyl ether, 97%

Chemical Property of (S)-2-(Bis(3,5-bis(trifluoromethyl)phenyl)((trimethylsilyl)oxy)methyl)pyrrolidine

Chemical Property:

• Melting Point: 48-56oC
• Boiling Point: 382.4±37.0 °C(Predicted)
• PKA: 9.34±0.10(Predicted)
• Flash Point: 110oC
• PSA: 21.26000
• Density: 1.319±0.06 g/cm3 (20 oC 760 Torr), Calc.*
• LogP: 8.93770
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 5
• Exact Mass: 597.1357288
• Heavy Atom Count: 39
• Complexity: 737

Purity/Quality:

98%,99%, ^*data from raw suppliers

(S)-α,α-Bis[3,5-di(trifluoromethyl)phenyl]-O-(trimethylsilyl)pyrrolidine-2-methanol ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)OC(C1CCCN1)(C2=CC(=CC(=C2)C(F)(F)F)C(F)(F)F)C3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F
• Isomeric SMILES: C[Si](C)(C)OC([C@@H]1CCCN1)(C2=CC(=CC(=C2)C(F)(F)F)C(F)(F)F)C3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F
• Uses: (S)-α,α-Bis[3,5-di(trifluoromethyl)phenyl]-O-(trimethylsilyl)pyrrolidine-2-methanol, is a diarylprolinol silyl ether organocatalyst. It is able to catalyze a variety of bond-forming reactions such as C-C, C-N, C-O, C-S, and C-Hal in high yields and excellent levels of enantiocontrol.

Technology Process of (S)-2-(Bis(3,5-bis(trifluoromethyl)phenyl)((trimethylsilyl)oxy)methyl)pyrrolidine

There total 4 articles about (S)-2-(Bis(3,5-bis(trifluoromethyl)phenyl)((trimethylsilyl)oxy)methyl)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: 100.0%

(S)-(-)-α,α-bis[3,5-bis(trifluoromethyl)phenyl]-2-pyrrolidinemethanol (848821-76-1) + trimethylsilyl trifluoromethanesulfonate (27607-77-8) → (S)-2-{bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilanyl)oxy]methyl}pyrrolidine (848821-61-4)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1002/anie.200462101

Reference yield:

C29H31F12NOSi (1608182-01-9) → (S)-2-{bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilanyl)oxy]methyl}pyrrolidine (848821-61-4) + isovaleraldehyde (590-86-3)

Guidance literature:

In [D₃]acetonitrile; Solvent; Equilibrium constant;

DOI:10.1021/ol501044u

Reference yield:

C28H29F12NOSi → (S)-2-{bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilanyl)oxy]methyl}pyrrolidine (848821-61-4) + butyraldehyde (123-72-8)

Guidance literature:

With water; In [D₃]acetonitrile; Equilibrium constant;

DOI:10.1021/jacs.6b04871

upstream raw materials:

(S)-(-)-α,α-bis[3,5-bis(trifluoromethyl)phenyl]-2-pyrrolidinemethanol

trimethylsilyl trifluoromethanesulfonate

C₂₉H₃₁F₁₂NOSi

Downstream raw materials:

C₂₉H₃₁F₁₂NOSi

Refernces

• 1、 Boeckman, Robert K.,Biegasiewicz, Kyle F.,Tusch, Douglas J.,Miller, John R.. "Organocatalytic enantioselective α-hydroxymethylation of aldehydes: Mechanistic aspects and optimization". . p. 4030 - 4045. Retrieved 2015/05/05.
• 2、 Marigo, Mauro,Wabnitz, Tobias C.,Fielenbach, Doris,Jorgensen, Karl Anker. "Enantioselective organocatalyzed α sulfenylation of aldehydes". . p. 794 - 797. Retrieved 2007/10/03.