Sodium borohydride → [(2R,3R,4R)-2-[(1R)-1-(3,5-Bis(trifluoromethyl)phenyl)ethoxy]-3-(3,4-difluorophenyl)-tetrahydropyran-4-yl]methanol

HRID 747002Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 747002
[BH4-].[Na+].[F:3][C:4]([F:35])([F:34])[C:5]1[CH:6]=[C:7]([C@H:15]([O:17][C@@H:18]2[C@@H:23]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[C:26]([F:31])[CH:25]=3)[C@H:22]([CH:32]=[O:33])[CH2:21][CH2:20][O:19]2)[CH3:16])[CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1>CO>[F:35][C:4]([F:3])([F:34])[C:5]1[CH:6]=[C:7]([C@H:15]([O:17][C@@H:18]2[C@@H:23]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[C:26]([F:31])[CH:25]=3)[C@H:22]([CH2:32][OH:33])[CH2:21][CH2:20][O:19]2)[CH3:16])[CH:8]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:10]=1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 86601747(2R,3R,4R)-2-[(1R)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxy]-3-(3,4-difluorophenyl)-tetrahydropyran-4-carbaldehyde

Produkt 1

HCID 11420320[(2R,3R,4R)-2-[(1R)-1-(3,5-Bis(trifluoromethyl)phenyl)ethoxy]-3-(3,4-difluorophenyl)-tetrahydropyran-4-yl]methanolAusbeute 93,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Sodium borohydride (24 mg, 0.63 mmol) was added to solution of 2-[1-{(2R,3R,4R)-2-[(1R)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxy]-3-(3,4-difluorophenyl)-tetrahydropyran-4-carbaldehyde (see Example 2 in WO 02/16344; 107 mg, 0.23 mmol) in methanol (3 ml). The mixture was stirred for 30 minutes then quenched with saturated aqueous NaHCO3 and extracted into ethyl acetate. The combined organic extracts were dried and concentrated to give the title compound (104 mg).

Aufarbeitung

  1. customthen quenched with saturated aqueous NaHCO3
  2. extractionextracted into ethyl acetate
  3. customThe combined organic extracts were dried
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-7a72c20896614903831681d05465cae7
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07393858B2

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