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

CAS No.112068-01-6
Chemical Name:(S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol
CBNumber:CB5178203
Molecular Formula:C17H19NO
Formula Weight:253.34
MOL File:112068-01-6.mol

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

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)
FDA UNII K3HE3KC32M
NIST Chemistry Reference S-(-)-1,1-diphenylprolinol(112068-01-6)
UNSPSC Code 12352005
NACRES NA.22

Safety

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

NFPA 704:

	1
2		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H315-H319-H335
Precautionary statements P261-P264-P271-P280-P302+P352-P305+P351+P338

(S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol Price More Price(4)

Brand: Sigma-Aldrich(India)
Product number: 368199
Product name : (S)-(−)-α,α-Diphenyl-2-pyrrolidinemethanol
Purity: 99%
Packaging: 1G
Price: ₹4308.35
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: 368199
Product name : (S)-(−)-α,α-Diphenyl-2-pyrrolidinemethanol
Purity: 99%
Packaging: 5G
Price: ₹10944.08
Updated: 2022/06/14
Buy: Buy

Brand: TCI Chemicals (India)
Product number: D2735
Product name : (S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol
Purity: min. 98.0 %
Packaging: 1G
Price: ₹4700
Updated: 2022/05/26
Buy: Buy

Brand: TCI Chemicals (India)
Product number: D2735
Product name : (S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol
Purity: min. 98.0 %
Packaging: 5G
Price: ₹15000
Updated: 2022/05/26
Buy: Buy

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

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.