(R)-(+)-a,a-Diphenyl-2-pyrrolidinemethanol RC00261

Manufacturer: Hangzhou Royalchem Co.,LTD.

Website:   www.cnroyalchem.com

Here is a detailed product description for   (R)-(+)-α,α-Diphenyl-2-pyrrolidinemethanol  (CAS 22348-32-9):

1. Product Identification:  *  Chemical Name:  (R)-(+)-α,α-Diphenyl-2-pyrrolidinemethanol *  Synonyms:  * (R)-(+)-2-(Diphenylhydroxymethyl)pyrrolidine * (R)-(+)-α,α-Diphenyl-2-pyrrolidinemethanol * (R)-(−)-CBS Catalyst precursor (Note: The active catalyst is the  in situ  formed oxazaborolidine) * (R)-CBS Reagent part A * (R)-Diphenylprolinol *  CAS Registry Number:  22348-32-9 *  Molecular Formula:  C₁₇H₁₉NO *  Molecular Weight:  253.34 g/mol *  Optical Rotation:  Typically [α]²⁵D = +36° to +42° (c=1, CHCl₃) for the enantiomerically pure compound. *  Enantiomeric Excess (ee):  Typically supplied as ≥98% ee or ≥99% ee by chiral HPLC.

2. Structural Characteristics:  *  Core Structure:  Pyrrolidine ring (5-membered saturated nitrogen heterocycle). *  Key Functional Groups:  * Secondary amine (-NH-) on the pyrrolidine ring. * Chiral tertiary alcohol (-C(OH)Ph₂) attached directly to the alpha carbon of the pyrrolidine ring. *  Chirality:  Contains one stereogenic center (the carbon bearing the hydroxyl and diphenylmethyl groups). This product is the  (R)-enantiomer , which is dextrorotatory (+), indicated by the (+)- prefix or (R)- designation.

3. Primary Application:  *  Organocatalyst Precursor:  This compound's most significant role is as the  precursor to the highly effective (R)-CBS Catalyst  (Corey-Bakshi-Shibata Catalyst). *  CBS Catalyst Formation:  It reacts  in situ  with borane (BH₃) or borane derivatives (e.g., BH₃·THF, BH₃·SMe₂, catecholborane) to form the corresponding  (R)-oxazaborolidine  catalyst. *  Function of CBS Catalyst:  The (R)-oxazaborolidine catalyst is a powerful chiral Lewis acid catalyst used for the  highly enantioselective reduction of prochiral ketones  to secondary alcohols using borane (BH₃) as the stoichiometric reductant. *  Substrate Scope:  Especially effective for aryl alkyl ketones, α,β-unsaturated enones, and certain other ketone types. *  Enantioselectivity:  Delivers secondary alcohols with excellent enantiomeric excesses (ee), often >95% and frequently >99%. *  Chirality Transfer:  The (R)-configuration of the precursor dictates that the CBS catalyst delivers the (S)-alcohol from most prochiral ketones (and the (R)-alcohol from α-halo ketones). *  Mode of Action:  The chiral oxazaborolidine activates and directs the delivery of borane (BH₃) to one face of the ketone carbonyl group through a well-defined six-membered transition state involving coordination of the carbonyl oxygen to the boron atom.

4. Physical Properties:  *  Appearance:  Typically supplied as a white to off-white crystalline solid or powder. *  Melting Point:  Approximately 83-87 °C. *  Solubility:  * Soluble in common organic solvents: Dichloromethane (DCM), chloroform (CHCl₃), tetrahydrofuran (THF), diethyl ether, ethyl acetate, toluene. * Moderately soluble in alcohols (methanol, ethanol, isopropanol). * Sparingly soluble or insoluble in water and aliphatic hydrocarbons (hexane, pentane). *  Storage:  Store in a cool (2-8°C), dry place under an inert atmosphere (Argon or Nitrogen) to minimize oxidation and moisture uptake. Keep tightly sealed. 

5. Chemical Properties & Reactivity:  *  Basic Nature:  The pyrrolidine nitrogen is a moderately strong base and a nucleophile. *  Hydrogen Bonding:  The alcohol (-OH) acts as a hydrogen bond donor, and the amine (-NH-) can act as both a donor and acceptor. These groups are crucial for its coordination to boron in forming the active catalyst. *  Chirality Source:  The rigid chiral environment created by the pyrrolidine ring and the bulky diphenylhydroxymethyl group is essential for inducing high enantioselectivity in the CBS-catalyzed reductions. *  Oxidation Sensitivity:  The tertiary alcohol is generally stable, but the secondary amine can be sensitive to oxidation over time, especially if exposed to air. 

6. Quality Specifications (Typical Commercial Lot):  *  Purity (HPLC/GC):  ≥98% area *  Enantiomeric Excess (ee):  ≥98% ee (determined by chiral HPLC) *  Water Content (KF):  ≤0.5% w/w (often much lower, stored under N₂/Ar) *  Residual Solvents:  Meets ICH limits (e.g., <5000 ppm total solvents, specific limits for common solvents like hexanes, EtOAc, alcohols). *  Confirmation:  Identity typically confirmed by ¹H NMR, ¹³C NMR, FT-IR, and optical rotation. Purity and ee by HPLC.

7. Handling and Safety:  *  Hazard Classification:  Generally classified as  Harmful (H302, H312, H315, H319, H332, H335) . Specific classifications vary by supplier and region. Consult the Safety Data Sheet (SDS) for the exact lot. *  Key Hazards:  * Harmful if swallowed (H302). * Harmful in contact with skin (H312). * Causes skin irritation (H315). * Causes serious eye irritation (H319). * Harmful if inhaled (H332). * May cause respiratory irritation (H335). *  Precautions:  *  Personal Protection:  Wear appropriate protective gloves (e.g., nitrile), eye/face protection (safety goggles), and lab coat. Use adequate ventilation (fume hood). *  Avoid Contact:  Avoid breathing dust/fume/mist/spray. Avoid contact with skin, eyes, and clothing. *  Incompatibilities:  Strong oxidizing agents. *  Hygiene:  Wash thoroughly after handling. *  First Aid:  See specific SDS details. Generally: Eye contact - rinse cautiously with water for several minutes. Skin contact - wash with soap and water. Inhalation - move to fresh air. Ingestion - rinse mouth, do NOT induce vomiting, seek medical advice.