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

Melting point:

113-117 °C

Boiling point:

391.8±42.0 °C(Predicted)

Density 

1.465±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

12.26±0.29(Predicted)

form 

powder to crystal

color 

White to Light yellow

optical activity

-52.535°(C=0.01g/ml CHCL3)

InChI

InChI=1/C21H15F12NO/c22-18(23,24)12-4-10(5-13(8-12)19(25,26)27)17(35,16-2-1-3-34-16)11-6-14(20(28,29)30)9-15(7-11)21(31,32)33/h4-9,16,34-35H,1-3H2/t16-/s3

InChIKey

ITXPGQOGEYWAKW-INIZCTEOSA-N

SMILES

C(F)(F)(C1=CC(C(O)(C2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)[C@@H]2CCCN2)=CC(=C1)C(F)(F)F)F |&1:22,r|

Safety Information

WGK Germany 

3

HS Code 

2933.99.8290

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

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

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