(S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol RC00266

Manufacturer: Hangzhou Royalchem Co.,LTD.

Website:   www.cnroyalchem.com

【 Providing a complete set of intermediates and impurities for Dapoxetine 】

【 Providing a complete set of intermediates and impurities for Dapoxetine 】

【 Providing a complete set of intermediates and impurities for Dapoxetine 】

Here is a detailed product description for  112068-01-6 (S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol :

Product Identification

CAS Registry Number:  112068-01-6

Chemical Name:  (S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol

Synonyms:

(S)-(-)-2-(Diphenylhydroxymethyl)pyrrolidine

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

(S)-(-)-DPPMP (common abbreviation)

(S)-(-)-α,α-Diphenylpyrrolidine-2-methanol

(S)-Pyrrolidine Methanol, α,α-diphenyl-

Molecular Formula:  C₁₇H₁₉NO

Molecular Weight:  253.34 g/mol

Structural Characteristics

Core Structure:  Features a pyrrolidine ring (a 5-membered nitrogen heterocycle) substituted at the 2-position with a methanolic group (-CH₂OH).

Chiral Center:  The carbon atom bearing the hydroxymethyl group and attached to the pyrrolidine ring is a stereogenic center. This compound is the  (S)-enantiomer .

Diphenyl Groups:  Two phenyl groups are attached to the same chiral carbon as the hydroxymethyl group, making it a tertiary alcohol.

Specific Rotation:  Typically denoted as  (S)-(-)- , indicating it is the levorotatory enantiomer. The specific rotation value is usually provided by the supplier (e.g., [α]D²⁵ ~ -33° to -38° (c=1-2 in ethanol or methanol), but exact values depend on solvent and concentration).

Physical Properties

Appearance:  Typically a white to off-white crystalline solid or powder.

Melting Point:  Approximately 70-74 °C (reported values can vary slightly).

Solubility:

Soluble in common organic solvents like ethanol, methanol, acetone, chloroform, dichloromethane, ethyl acetate, and toluene.

Generally insoluble in water.

Hygroscopicity:  May exhibit slight hygroscopic properties; store under inert atmosphere.

Key Applications & Significance

Chiral Auxiliary/Inducer/Catalyst:

Highly Valued:  Primarily used as a  chiral auxiliary  in asymmetric synthesis.

Mechanism:  The pyrrolidine nitrogen and the chiral tertiary alcohol group can coordinate with metals or form intermediates, directing the stereochemical outcome of reactions.

Reactions:  Employed in enantioselective additions (e.g., alkylations, aldol reactions), reductions, and other transformations to create new chiral centers with high enantiomeric excess (ee).

Pharmaceutical Intermediate (Key Role):

Critical Precursor:  This specific (S)-enantiomer is the  essential chiral building block  for the synthesis of  (S)-Duloxetine hydrochloride , a widely prescribed medication.

Duloxetine:  Marketed under brands like  Cymbalta®  and  Yentreve® , it is a potent Serotonin-Norepinephrine Reuptake Inhibitor (SNRI) used to treat major depressive disorder (MDD), generalized anxiety disorder (GAD), diabetic peripheral neuropathic pain (DPNP), fibromyalgia, and chronic musculoskeletal pain.

Synthetic Route:  In the synthesis of Duloxetine, (S)-DPPMP acts as the chiral source. It is typically converted into the corresponding (S)-N-methylamino alcohol derivative via processes like methylation of the nitrogen and then used in a resolution or direct asymmetric synthesis step.

Building Block:  Useful in the synthesis of other complex chiral molecules requiring a diphenyl-substituted pyrrolidinylmethanol unit.

Handling and Storage

Storage Conditions:  Store in a cool (2-8°C), dry place. Store under an inert atmosphere (Argon or Nitrogen) to prevent oxidation and moisture absorption. Keep container tightly sealed.

Stability:  Stable under recommended storage conditions. May be sensitive to prolonged exposure to light, air, and moisture.

Handling:  Handle using standard laboratory safety practices. Use in a well-ventilated area (fume hood). Avoid contact with skin, eyes, and clothing. Avoid breathing dust.

Safety:  Refer to the Safety Data Sheet (SDS) for specific hazards, first aid measures, and handling procedures. Generally considered harmful if swallowed, causes skin and eye irritation, and may cause respiratory irritation (H302, H315, H319, H335). Appropriate PPE (gloves, safety glasses, lab coat) is essential.