368199

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

99%

• Synonym(s): (S)-(−)-2-(Diphenylhydroxymethyl)pyrrolidine, α,α-Diphenyl-L-prolinol
• Empirical Formula (Hill Notation): C₁₇H₁₉NO
• CAS Number: 112068-01-6
• Molecular Weight: 253.34
• MDL number: MFCD00075506
• UNSPSC Code: 12352005
• PubChem Substance ID: 24862899
• NACRES: NA.22

Properties

• Assay: 99%
• form: solid
• optical activity: [α]20/D −67°, c = 3 in chloroform
• mp: 77-80 °C (lit.)
• functional group: hydroxyl; phenyl
• SMILES string: OC([C@@H]1CCCN1)(c2ccccc2)c3ccccc3
• InChI: 1S/C17H19NO/c19-17(16-12-7-13-18-16,14-8-3-1-4-9-14)15-10-5-2-6-11-15/h1-6,8-11,16,18-19H,7,12-13H2/t16-/m0/s1
• InChI key: OGCGXUGBDJGFFY-INIZCTEOSA-N

Description

General description

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

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.

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H315,H319,H335
• Precautionary Statements: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves