D-Alanine,N-[3-chloro-4-(trifluoromethyl)phenyl]- → (R)-2-(3-Chloro-4-trifluoromethyl-phenylamino)-propan-1-ol

20.55 ml (20.55 mmol, 1 M in THF) of a borane-tetrahydrofuran complex solution was added dropwise at 0° C. to a solution of 2.20 g (8.20 mmol) of (R)-2-(3-chloro-4-trifluoromethyl-phenylamino)-propionic acid (22% ee) in 33 ml THF, then after 10 min the ice bath was removed and the solution stirred for 2.5 h at RT. After cooling, 14 ml of MeOH and 0.7 ml of H2SO4 were added, and after 30 min at RT and 1 h at reflux the reaction mixture was concentrated in vacuo. The residue was partitioned between 1 M aq. sodium hydroxide saturated with NaCl solution and EtOAc (3×). The organic layer was washed with brine, dried (Na2SO4), filtered, and evaporated. Flash silica gel column (CH2Cl2/MeOH 99:1) afforded 1.94 g (93%) of the title compound as a 61:39 mixture of the (R) and (S) stereoisomers as yellow oil. MS: 252.04 (M−H−, Cl)

1. customafter 10 min the ice bath was removed
2. temperatureAfter cooling
3. addition14 ml of MeOH and 0.7 ml of H2SO4 were added
4. waitafter 30 min at RT
5. temperature1 h at reflux the reaction mixture
6. concentrationwas concentrated in vacuo
7. customThe residue was partitioned between 1 M aq. sodium hydroxide saturated with NaCl solution and EtOAc (3×)
8. washThe organic layer was washed with brine
9. dry with materialdried (Na2SO4)
10. filtrationfiltered
11. customevaporated

ORD 기록

ord-ef0d0dd8bbd24c10ba1745df8beb7670

출처 데이터셋

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08445674B2