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(R)-(+)-α,α-Diphenyl-2-pyrrolidinemethanol Trimethylsilyl Ether
(CAS RN: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
Synonym (R)-Hayashi-Jorgensen Catalyst

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 RN 943757-71-9
Related CAS RN
MDL Number MFCD09265100
  • Product Details
  • Safety & Regulations
  • Reference & Application

Specification

Appearance Light orange to Yellow to Green clear liquid
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
PubChem SID 354334881

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 soap and 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 2933.99.8290

Application

Organocatalysts for Asymmetric Michael Additional Reactions

D3843_D3867

References

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

PubMed Literature

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