Hydrochloric Acid → [(4R,5R)-5-(4-methylsulfonylphenyl)-2-phenyl-4,5-dihydro-1,3-oxazol-4-yl]methanol

HRID 1879336Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1879336
C([O:3][C:4]([C@@H:6]1[C@@H:10]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=2)[O:9][C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:7]1)=O)C.[BH4-].[K+].Cl.O>CO>[CH3:20][S:17]([C:14]1[CH:13]=[CH:12][C:11]([C@H:10]2[O:9][C:8]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N:7][C@@H:6]2[CH2:4][OH:3])=[CH:16][CH:15]=1)(=[O:18])=[O:19]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4192641Potassium borohydrideHCID 46831018(4S-trans)-4,5-dihydro-5-[4-(methylsulfonyl)phenyl]-2-phenyl-4-oxazolecarboxylic acid ethyl ester

Produkt 1

HCID 14760452[(4R,5R)-5-(4-methylsulfonylphenyl)-2-phenyl-4,5-dihydro-1,3-oxazol-4-yl]methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

(4S-trans)-4,5-Dihydro-5-[4-(methylsulfonyl)phenyl]-2-phenyl-4-oxazolecarboxylic acid ethyl ester (Compound IIIk) (about 5 g, 0.0134 moles) in methanol (about 50 mL) is reacted in a reaction vessel with potassium borohydride (about 1.1 g, 0.0201 moles) over about 6 hours while maintaining the temperature below about 60° C. The reaction is cooled to ambient room temperature and about 1N HCl (about 10 mL) and water (about 50 mL) are added. The resulting solids are filtered, washed with water, then dried to yield (4R,5R)-4,5-Dihydro-5-[4-(methylsulfonyl)phenyl]-2-phenyl-4-oxazolemethanol (Compound II wherein R1 is methylsulfonyl, R2 is phenyl and R3 is ethyl).

Aufarbeitung

  1. temperaturewhile maintaining the temperature below about 60° C
  2. filtrationThe resulting solids are filtered
  3. washwashed with water
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-7a6fb71739e2406fafd86c65e7bb3ab7
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08314252B2

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