CAS 112068-01-6 (S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol

Synonyms

TL8000351; S)-(-)-A,A-Diphenyl-2-pyrrolidinemethanol; ACN-036587; AK-40863; DTXSID50369275; ST24032110; (S)-(-)-Diphenylpyrrolidinemethanol; CS-D1383; BR-40863; Jsp000919;

IUPAC Name

diphenyl-[(2S)-pyrrolidin-2-yl]methanol;

Molecular Weight

253.345g/mol

Molecular Formula

C17H19NO;

Canonical SMILES

C1CC(NC1)C(C2=CC=CC=C2)(C3=CC=CC=C3)O;

InChI

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;

Storage

Store below +30°C.

Complexity

261

Covalently-Bonded Unit Count

Defined Atom Stereocenter Count

EC Number

601-153-1

Exact Mass

253.147g/mol

H-Bond Acceptor

H-Bond Donor

Heavy Atom Count

Monoisotopic Mass

253.147g/mol

Rotatable Bond Count

Topological Polar Surface Area

32.3A^2

Application

(S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol, characterized by its white to beige crystalline form, serves as a versatile bifunctional organocatalyst with several critical applications in asymmetric synthesis. Primarily, it is employed in the formation of oxazaborolidines, which facilitate borane-mediated asymmetric ketone reductions. This compound can react with catecholborane to produce a spiroborate ester, effectively catalyzing the synthesis of enantiopure alcohols through the borane reduction of acetophenone. Additionally, when combined with borane-diethylaniline, it forms a catalyst that proficiently drives the enantioselective reduction of 2'-fluoroacetophenone. Moreover, the utilization of mesoporous SBA-15 silica functionalized with this compound can catalyze the reaction of diethylzinc with benzaldehyde to yield (S)-1-phenyl-propanol, showcasing its adaptability and efficiency in various catalytic transformations.

February 19, 2025

Excellent Catalyst for Asymmetric Reductions

Used (S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol to efficiently catalyze enantioselective reductions in our lab. The crystals dissolve well in reactions, promoting high yields of enantiopure alcohols. Highly recommended for precise applications!