(S)-2-{Bis[3,5-bis(trifluoromethyl)phenyl]hydroxymethyl}pyrrolidine

Uses

(S)-2-{Bis[3,5-bis(trifluoromethyl)phenyl]hydroxymethyl}pyrrolidine is a chiral ligand, used in catalytic asymmetric synthesis. Its application extends to the production of propargylic sulfamidates and cyclic imines.

Synthesis

The general procedure for the synthesis of S-α,α-bis(3,5-bis-trifluoromethyl-phenyl)proline from the compound (CAS: 845965-28-8) was as follows: 4.3 g (76 mmol) of KOH and 4.2 g (7.6 mmol) of (S)-1,2-bis-(3,5-bis-trifluoromethyl-phenyl)-tetrahydro-pyrrolo[1,2-c]oxazole -3- was suspended in 20 mL of methanol and heated to reflux for 2 hours. After completion of the reaction, it was cooled to room temperature and the solvent was removed under reduced pressure. After addition of water, the mixture was extracted with dichloromethane. The organic phase was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure to give 4.2 g (99% yield) of the target product as a colorless oil.

References

[1] Patent: WO2005/80298, 2005, A1. Location in patent: Page/Page column 31