Ethanol → 3,3,3-Trifluoro-2-(trifluoromethyl)-1-(hydroxymethyl)propylamine

Temperature

25 °C

A solution of 4,4,4,4′,4′,4′-hexafluoro-DL-valine (0.500 g, 2.22 mmol) in THF (20 mL) was stirred under nitrogen at 25° C. Borane-THF complex (6.66 mL, 1.0 M in THF) was added dropwise and the resulting solution stirred for 4 h at 25° C. After this time period, the reaction was complete by TLC (10:2:1 EtOAc:EtOH:H2O). The reaction mixture was quenched by slow addition of 10% HOAc in MeOH (23 mL). After concentration, the residue was dissolved in Et2O (200 mL) and washed with saturated aqueous NaHCO3 (3×20 mL) and brine (20 mL), and then dried using Na2SO4. After concentration, the resulting residue was used directly in the next reaction without further purification.

1. customThe reaction mixture was quenched by slow addition of 10% HOAc in MeOH (23 mL)
2. concentrationAfter concentration
3. dissolutionthe residue was dissolved in Et2O (200 mL)
4. washwashed with saturated aqueous NaHCO3 (3×20 mL) and brine (20 mL)
5. customdried
6. concentrationAfter concentration
7. customthe resulting residue was used directly in the next reaction without further purification

ORD record

ord-bd5fa1ac19e647339eae81a8b406f37b

Source dataset

uspto-grants-2007_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07300951B2