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(R)-(+)-α,α-Diphenyl-2-pyrrolidinemethanol Trimethylsilyl Ether
(CAS Number:943757-71-9 Product Number:D3867)

Structure

(R)-(+)-alpha,alpha-Diphenyl-2-pyrrolidinemethanol Trimethylsilyl Ether
Synonym α,α-Diphenyl-D-prolinol Trimethylsilyl Ether
Synonym (R)-(+)-2-[Diphenyl(trimethylsilyloxy)methyl]pyrrolidine

General Information

Product Number D3867

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Purity/Analysis Method >98.0%(GC)(T)
Storage Temperature 0-10°C
M.F. / M.W. C20H27NOSi=325.53
CAS Number 943757-71-9
Related CAS Number
MDL Number MFCD09265100
Packaging and Container
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Specification

Specific rotation(value) 53.0 to 57.0 deg
Purity(GC) min. 98.0 %
Purity(Nonaqueous Titration) min. 98.0 %
Specific gravity (20/20) 1.0410 to 1.0450
Refractive index n20/D 1.5480 to 1.5520
Specific rotation [a]20/D +53.0 to +57.0 deg(C=1, CHCl3)

References

Reaxys-RN 15634082

GHS

Pictogram
Signal Word Warning
Hazard Statements
  • H315
  • :Causes skin irritation.
  • H319
  • :Causes serious eye irritation.
Precautionary Statements
  • P264
  • :Wash hands and face thoroughly after handling.
  • P280
  • :Wear protective gloves, eye protection.
  • P302+P352+P332+P313+P362+P364
  • :IF ON SKIN: Wash with plenty of water. If skin irritation occurs: Get medical advice or attention. Take off contaminated clothing and wash it before reuse.
  • P305+P351+P338+P337+P313
  • :IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. If eye irritation persists: Get medical advice or attention.

Transport Information

HS Number 2933998090

Application

Asymmetric Organocatalyst

Experimental procedure3): Chloroacetic acid (21.8 mg, 0.231 mmol) is added to a solution of 1 (225 mg, 1.73 mmol), 2 (200 mg, 1.16 mmol) and 3 (18.8 mg, 0.058 mmol) in CH2Cl2 (2 mL) at 23 °C under Ar atmosphere. The reaction mixture is stirred for 40 min at 23 °C followed by addition of 4 (409.2 mg, 1.73 mmol) and Cs2CO3 (1.13 g, 3.47 mmol) at 0 °C. After the resulting suspension is stirred for additional 3 h at 0 °C, the solvent is removed under reduced pressure at 0 °C. EtOH (3 mL) is added to the crude mixture. The resulting mixture is stirred for 15 min at 23 °C before addition of p-toluenethiol (716.7 mg, 5.78 mmol) at –15 °C. The resulting mixture is stirred for 36 h at same temperature before being quenched with cold 2 mol/L HCl. The aqueous layer is extracted three times with CHCl3. The combined organic layer is washed with saturated aqueous NaHCO3, dried over MgSO4, and concentrated under reduced pressure. Flash chromatography (SiO2, EtOAc:hexane = 5:95 – 10:90) provides 5 (413.7 mg, 70%) as colorless oil.

References

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