Acetic Acid → (2R)-2-[({6-[4-fluoro-3-(trifluoromethyl)phenyl]pyridin-2-yl}methyl)amino]-3-methylbutan-1-ol

HRID 1472924Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1472924
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([CH:14]=O)[CH:11]=[CH:10][CH:9]=2)=[CH:4][C:3]=1[C:16]([F:19])([F:18])[F:17].[NH2:20][C@@H:21]([CH2:25][OH:26])[CH:22]([CH3:24])[CH3:23].C(O)(=O)C.C([BH3-])#N>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([CH2:14][NH:20][C@H:21]([CH:22]([CH3:24])[CH3:23])[CH2:25][OH:26])[CH:11]=[CH:10][CH:9]=2)=[CH:4][C:3]=1[C:16]([F:19])([F:18])[F:17]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 498716Cyano-borohydrideHCID 6950587D-ValinolHCID 848199696-(4-Fluoro-3-(trifluoromethyl)phenyl)picolinaldehyde

Produkt 1

HCID 68312365(2R)-2-[({6-[4-fluoro-3-(trifluoromethyl)phenyl]pyridin-2-yl}methyl)amino]-3-methylbutan-1-olAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of Example 267A (0.500 g, 1.86 mmol) in methanol (20 mL) at ambient temperature was added D-valinol (0.20 mL, 1.9 mmol) and acetic acid (0.40 mL, 7.4 mmol) followed by MP-cyanoborohydride (2.49 mmol/g; 1.0 g). After 2 hours, the mixture was filtered, concentrated and the residue partitioned between ether and 1M NaOH. The organic extract was concentrated and purified by chromatography to provide 390 mg (59%) of the title compound. MS (DCI+) m/z 270 (M+H); 1H NMR (500 MHz, CDCl3) δ 8.28 (dd, J=6.8, 2.0 Hz, 1H), 8.24-8.15 (m, 1H), 7.76 (t, J=7.7 Hz, 1H), 7.61 (d, J=7.8 Hz, 1H), 7.34-7.25 (m, 2H), 4.04 (q, J=14.5 Hz, 2H), 3.70 (dd, J=10.9, 4.0 Hz, 1H), 3.49 (dd, J=10.8, 6.9 Hz, 1H), 2.53 (td, J=6.7, 4.1 Hz, 1H), 1.97-1.85 (m, 1H), 1.04 (d, J=6.8 Hz, 3H), 0.97 (d, J=6.9 Hz, 3H).

Aufarbeitung

  1. filtrationthe mixture was filtered
  2. concentrationconcentrated
  3. customthe residue partitioned between ether and 1M NaOH
  4. extractionThe organic extract
  5. concentrationwas concentrated
  6. custompurified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d364635489bd4bcd967dadf304a741d0
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09012651B2

Notizen zur Reaktion

Wird geladen…