(S)-(-)-ALPHA,ALPHA-DIPHENYL-2-PYRROLIDINYL METHYLTMS ETHER Chemical Properties

Boiling point:

412.7±35.0 °C(Predicted)

Density 

1.0459 g/mL at 25 °C

refractive index 

n20/D 1.5513

Flash point:

110 °C

storage temp. 

2-8°C

pka

10.01±0.10(Predicted)

form 

liquid

color 

Yellow

optical activity

[α]22/D -50°, c = 1 in chloroform

Hydrolytic Sensitivity

7: reacts slowly with moisture/water

λmax

193nm(lit.)

InChI

InChI=1S/C20H27NOSi/c1-23(2,3)22-20(19-15-10-16-21-19,17-11-6-4-7-12-17)18-13-8-5-9-14-18/h4-9,11-14,19,21H,10,15-16H2,1-3H3/t19-/m0/s1

InChIKey

RSUHWMSTWSSNOW-IBGZPJMESA-N

SMILES

N1CCC[C@H]1C(C1=CC=CC=C1)(C1=CC=CC=C1)O[Si](C)(C)C

Safety Information

Hazard Codes 

Xi,Xn,F

Risk Statements 

36/37/38-67-65-48/20-38-11-63

Safety Statements 

26-62-36/37-16

RIDADR 

UN1294 - class 3 - PG 2 - Toluene, solution

WGK Germany 

3

TSCA 

No

HS Code 

29339900

(S)-(-)-ALPHA,ALPHA-DIPHENYL-2-PYRROLIDINYL METHYLTMS ETHER Usage And Synthesis

Chemical Properties

Light yellow liquid

Uses

Organocatalyst for 3-component reactions, and Robinson annulation of α,β-unsaturated aldehydes.

Synthesis

To a solution of (S)-diphenylprolinol (4.00 g, 15.8 mmol, 1.00 eq.) in dichloromethane (40 mL) was added imidazole (3.22 g, 47.4 mmol, 3.00 eq.) at 0 °C. Trimethylchlorosilane (5.00 mL, 39.5 mmol, 2.50 eq.) was added slowly and the reaction mixture was subsequently stirred at room temperature for 12 hours. Upon completion of the reaction, the reaction mixture was diluted by addition of methyl tert-butyl ether (MTBE, 100 mL) and filtered to remove insoluble material. The organic phase was washed sequentially with water (50 mL) and saturated aqueous sodium chloride solution (2 x 50 mL), dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the colorless oily product (2S)-2-[diphenyl[(trimethylsilyl ester)oxy]methyl]-pyrrolidine (11, 5.00 g, 15.3 mmol, 97% yield). The product was characterized by 1H NMR (400 MHz, CDCl3), 13C NMR (101 MHz, CDCl3) and HR-MS (ESI), and the data were consistent with the expected structure.

References

[1] Journal of the American Chemical Society, 2014, vol. 136, # 52, p. 18140 - 18148
[2] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 18, p. 4996 - 5001
[3] Angewandte Chemie - International Edition, 2005, vol. 44, # 27, p. 4212 - 4215
[4] Patent: WO2010/144293, 2010, A1. Location in patent: Page/Page column 29
[5] Journal of Organic Chemistry, 2010, vol. 75, # 22, p. 7829 - 7841

(S)-(-)-ALPHA,ALPHA-DIPHENYL-2-PYRROLIDINYL METHYLTMS ETHER(848821-58-9)Related Product Information

• S-2-[[[(1,1-diMethylethyl)diMethylsilyl]oxy]bis(3,5-diMethylphenyl)Methyl]-Pyrrolidine
• S-2-[bis[3,5-bis(trifluoroMethyl)phenyl] [(triethylsilyl)oxy]Methyl]-Pyrrolidine
• (S)-[(diphenyl)-t-butyldimethylsiloxymethyl]pyrrolidine
• (S)-2-{Bis[3,5-bis(trifluoromethyl)phenyl]hydroxymethyl}pyrrolidine
• S-2-[bis[3,5-bis(3,5-diMethylphenyl] [(triethylsilyl)oxy]Methyl]-Pyrrolidine
• S-2-[bis[3,5-bis(trifluoroMethyl)phenyl][[(1,1-diMethylethyl)diMethylsilyl]oxy]Methyl]-Pyrrolidine
• S-2-[diphenyl[(triethylsilyl)oxy]Methyl]-Pyrrolidine
• (S)-(-)-2-[Bis(3,5-dimethylphenyl)hydroxymethyl]pyrrolidine
• Pyrrolidine, 2-[bis(3,5-dimethylphenyl)[(trimethylsilyl)oxy]methyl]-, (2S)-
• Pyrrolidine, 2-[diphenyl[(trimethylsilyl)oxy]methyl]-, (2R)-
• (S)-2-[(Bis(3,5-bis(trifluoromethyl)phenyl)trimethylsilanyloxy)methyl]pyrrolidine, (S)-2-[(Bis(3,5-bis(trifluoromethyl)phenyl)trimethylsilyloxy)methyl]pyrrolidine, (S)-α,α-[3,5-Bis(trifluoromethyl)phenyl]prolinol trimethylsilyl ether
• (S)a,a-Bis(3,5-dimethylphenyl)prolinol trimethylsilyl ether hydrochloride, (S)-2-[Bis(3,5-dimethylphenyl)(trimethylsilyloxy)methyl]pyrrolidine hydrochloride
• (S)-2-DIPHENYLMETHYLPYRROLIDINE
• (S)-(-)-ALPHA,ALPHA-DIPHENYL-2-PYRROLIDINYL METHYLTMS ETHER
• (S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol