Sodium borohydride → (S)-N-(3,4-Dimethyl-phenyl)-2-(4-fluoro-phenyl)-2-hydroxy-N-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-acetamide

HRID 1094341

Reaktionsgleichung

Reaktionsgleichung von HRID 1094341
[CH3:1][C:2]1[CH:3]=[C:4]([N:9]([CH2:21][CH2:22][C:23]2[CH:24]=[N:25][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:27][CH:28]=2)[C:10](=[O:20])[C:11]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[O:12])[CH:5]=[CH:6][C:7]=1[CH3:8].[BH4-].[Na+]>CO>[CH3:1][C:2]1[CH:3]=[C:4]([N:9]([CH2:21][CH2:22][C:23]2[CH:24]=[N:25][C:26]([C:29]([F:31])([F:32])[F:30])=[CH:27][CH:28]=2)[C:10](=[O:20])[C@H:11]([C:13]2[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=2)[OH:12])[CH:5]=[CH:6][C:7]=1[CH3:8]

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 58007489N-(3,4-Dimethyl-phenyl)-2-(4-fluoro-phenyl)-2-oxo-N-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-acetamide

Produkt 1

HCID 44546250(S)-N-(3,4-Dimethyl-phenyl)-2-(4-fluoro-phenyl)-2-hydroxy-N-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-acetamideAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of N-(3,4-dimethyl-phenyl)-2-(4-fluoro-phenyl)-2-oxo-N-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-acetamide (515 mg, 1.16 mmol) was dissolved in MeOH (8 mL), cooled to 0° C. and treated with NaBH4 (88 mg, 2.33 mmol) and stirred for 12 h at ambient temperature. The reaction mixture was quenched with aqueous K2CO3 (2 M, 1 mL), concentrated, then redissolved in EtOAc (15 mL) and washed with aqueous K2CO3 (2 M, 3×15 mL). The combined aqueous layers were extracted with EtOAc (3×15 mL) and the combined organic layers dried over sodium sulfate. Concentration and purification by chromatography (SiO2, heptane:ethyl acetate=95:5 to 60:40) afforded the racemic compound (501 mg, 97%) as a lightyellow oil. Separation by chromatography on a chiral column provided the title compound as a colourless oil MS m/e: 447.2 [M+H]+ which crystallized upon standing.

Aufarbeitung

  1. customThe reaction mixture was quenched with aqueous K2CO3 (2 M, 1 mL)
  2. concentrationconcentrated
  3. dissolutionredissolved in EtOAc (15 mL)
  4. washwashed with aqueous K2CO3 (2 M, 3×15 mL)
  5. extractionThe combined aqueous layers were extracted with EtOAc (3×15 mL)
  6. dry with materialthe combined organic layers dried over sodium sulfate
  7. concentrationConcentration and purification by chromatography (SiO2, heptane:ethyl acetate=95:5 to 60:40)

Quellen und Nachweise

ORD-Eintrag
ord-666807874528473fb23a749e7ef89065
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08133909B2

Verknüpfte Notizen

Wird geladen…