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

Synonym(s):(S)-(−)-2-(Diphenylhydroxymethyl)pyrrolidine;α,α-Diphenyl-L-prolinol

CAS NO.：112068-01-6
Empirical Formula: C17H19NO
Molecular Weight: 253.34
MDL number: MFCD00075506
EINECS: 601-153-1
SAFETY DATA SHEET (SDS)
Update Date: 2025-10-25 08:05:52

(S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol Structural

What is (S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol?

Chemical properties

white to beige crystals or crystalline powder

The Uses of (S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol

suzuki reaction

The Uses of (S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol

(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%.

preparation of (S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol

General Description

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

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

Melting point:	77-80 °C(lit.)
Boiling point:	396.54°C (rough estimate)
alpha	-59 º (c=3, methanol 25 ºC)
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
CAS DataBase Reference	112068-01-6(CAS DataBase Reference)
NIST Chemistry Reference	S-(-)-1,1-diphenylprolinol(112068-01-6)

Safety information for (S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.