(S)-α,α-Diphenyl-2-Pyrrolidinemethanol: A Chemical Marvel

(S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol is a very important chiral β-amino alcohol catalyst precursor.

Uses

(S)-α,α-Diphenyl-2-Pyrrolidinemethanol has found numerous applications in various fields, primarily due to its chiral properties and reactivity. In the pharmaceutical industry, it serves as a valuable chiral building block for the synthesis of various drugs.

The catalyst generated in situ by reacting (S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol with borane-diethylaniline, can efficiently catalyze the enantioselective reduction of 2′-fluoroacetophenone.

Mesoporous SBA-15 silica functionalized with (S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol can catalyze the addition of diethylzinc to benzaldehyde to form (S)-1-phenyl-propanol.

Synthesis

Optically pure (S)-α,α-diphenyl-2-pyrrolidine methanol was prepared from L-proline via protection of the amino group, reaction with the Grignard reagents and deprotection of the amino-protected groups in 54.4% yield. The synthetic conditions to prepare (S)-α,α-diphenyl-2-pyrrolidinemethanol were optimised. Single crystal X-ray diffraction analysis revealed that the molecular structure of the compound was enantiomerically pure. The crystals are orthorhombic, space group P2(1)2(1)2(1).

Reference

[1] Kaufman T S, Ponzo V L, Zinczuk J. A TRIPHOSGENE-BASED SYNTHESIS OF (S)-α, α-DIPHENYL-2-PYRROLIDINEMETHANOL[J]. Organic preparations and procedures international, 1996, 28(4): 487-490.