| Identification | Back Directory | [Name]
(S)-(-)-ALPHA,ALPHA-DIPHENYL-2-PYRROLIDINYL METHYLTMS ETHER | [CAS]
848821-58-9 | [Synonyms]
(S)-(–
)-α,α-DiphenyL
(s)-(-)-
(S)-Hayashi-Jorgensen Catalyst
Jorgenson-Hayashi organocatalyst
S-Diphenylprolinol trimethyl silyl ether
[(DIPHENYL)TRIMETHYLSILOXYMETHYL]PYRROLIDINE
(S)-Diphenylprolinol Trimethyl Silyl Ether,99%e.e.
-diphenyl-2-pyrrolidine methanoltrimethylsilyl ether
(S)-(-)-[(DIPHENYL)TRIMETHYLSILOXYMETHYL]PYRROLIDINE
alpha,alpha-Diphenyl-L-prolinol Trimethylsilyl Ether
(S)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine
Diphenyl-(2S)-pyrrolidin-2-ylmethoxy-trimethyl-silane
(S)-2-[Diphenyl(Trimethylsilanyloxy)Methyl]Pyrrolidine
(S)-2-((2,2-diphenylethyl)diMethylsilyloxy)pyrrolidine
(2s)-2-[diphenyl[(trimethylsilyl)oxy]methyl]pyrrolidine
)-α,α-Diphenyl-2-pyrrolidinemethanol trimethylsilyl ether
(S)-(-)-ALPHA,ALPHA-DIPHENYL-2-PYRROLIDINYL METHYLTMS ETHER
(s)-(-)-lmdiphenyl-2-pyrrolidine methanoltrimethylsilyl ether
Pyrrolidine, 2-[diphenyl[(trimethylsilyl)oxy]methyl]-, (2S)-
(S)-(–)-α，α-Diphenyl-2-pyrrolidinemethanol trimethylsilyl ether
(S)-(-)-α,α-Diphenyl-2-pyrrolidoneMethanoe triMethylsilys ether
(s)-(-)-α,α-diphenyl-2-pyrrolidine methanol trimethylsilyl ether
(S)-(–)-α,α-Diphenyl-2-pyrrolidineMethanol triMethylsilyl ether 95%
(S)-()-α,α-Diphenyl-2-pyrrolidinemethanoltrimethylsilyl ether solution
(S)-(-)-alpha,alpha-Diphenyl-2-pyrrolidineMethanol triMethylsilyl ether 95%
(S)-(?)-α,α-Diphenyl-2-pyrrolidinemethanoltrimethylsilyl ether solution
(S)-(-)-ALPHA,ALPHA-DIPHENYL-2-PYRROLIDINEMETHANOL TRIMETHYLSILYL ETHER, 95%
(S)-(-)-alpha,alpha-Diphenyl-2-pyrrolidinemethanoltrimethylsilyl ether solution
(S)-()-α,α-Diphenyl-2-pyrrolidineMethanoltriMethylsilyl ether solution 0.05 M in toluene
(S)-(-)-alpha,alpha-Diphenyl-2-pyrrolidinemethanoltrimethylsilyl ether solution 0.05 M in toluene
(2S)-2-[Diphenyl[(trimethylsilyl)oxy]methyl]pyrrolidine, (S)-α,α-Diphenylprolinol trimethylsilyl ether, (S)-2-[Diphenyl(trimethylsilanyloxy)methyl]pyrrolidine | [Molecular Formula]
C20H27NOSi | [MDL Number]
MFCD08690083 | [MOL File]
848821-58-9.mol | [Molecular Weight]
325.52 |
| Chemical Properties | Back Directory | [Boiling point ]
412.7±35.0 °C(Predicted) | [density ]
1.0459 g/mL at 25 °C | [refractive index ]
n20/D 1.5513 | [Fp ]
110 °C | [storage temp. ]
2-8°C | [form ]
liquid | [pka]
10.01±0.10(Predicted) | [color ]
Yellow | [Optical Rotation]
[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 |
| Hazard Information | Back Directory | [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 |
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