(S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol Chemical Properties

Melting point:

77-80 °C(lit.)

alpha 

-59 º (c=3, methanol 25 ºC)

Boiling point:

396.54°C (rough estimate)

Density 

1.0078 (rough estimate)

refractive index 

-66.5 ° (C=3, CHCl3)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Soluble in chloroform.

form 

powder

pka

13.15±0.29(Predicted)

color 

white to off white ., crystal

optical activity

[α]20/D 67°, c = 3 in chloroform

Merck 

14,155

BRN 

17103

InChIKey

OGCGXUGBDJGFFY-INIZCTEOSA-N

CAS DataBase Reference

112068-01-6(CAS DataBase Reference)

NIST Chemistry Reference

S-(-)-1,1-diphenylprolinol(112068-01-6)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39-24/25-36

WGK Germany 

3

F 

10-34

TSCA 

No

HS Code 

29339900

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

(S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol Usage And Synthesis

Chemical Properties

white to beige crystals or crystalline powder

Uses

suzuki reaction

Uses

(S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol is used to prepare the corresponding oxazaborolidines for the borane-mediated asymmetric reduction of ketones.

Preparation

Into a four-necked flask, add tetrahydrofuran, L-proline methyl ester hydrochloride, and phenyl magnesium chloride （dissolved in tetrahydrofuran) solution was added dropwise from a constant pressure dropping funnel, and the addition was completed in about 4 hours, and then stirred at 10-15°C for 3 hours. Add water, adjust the pH to 5-6 with 10% ammonium chloride aqueous solution, extract with dichloromethane, extract the aqueous layer twice with dichloromethane each time, and obtain the organic phase. Wash once with saturated sodium chloride aqueous solution. The organic phase was dried with anhydrous sodium sulfate for 4 hours and filtered. The obtained organic phase was distilled under reduced pressure to distill dichloromethane and tetrahydrofuran to obtain light yellow oily (S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol, yield 86.6%.

Application

(S)-(+)-α,α-Diphenyl-2-pyrrolidinemethanol (DPPM) may be used in the following processes:

• DPPM reacts with catecholborane to form a spiroborate ester, which can be an efficient catalyst for the synthesis of enantiopure alcohols by borane reduction of acetophenone.

• The catalyst generated in situ by reacting DPPM with borane-diethylaniline, can efficiently catalyze the enantioselective reduction of 2′-fluoroacetophenone.

• Mesoporous SBA-15 silica functionalized with DPPM can catalyze the addition of diethylzinc to benzaldehyde to form (S)-1-phenyl-propanol.

Used to prepare the corresponding oxazaborolidines for the borane-mediated asymmetric reduction of ketones.

General Description

(S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol is a bifunctional organocatalyst.

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