Methanol → 4-[5-(2,4-Difluoro-phenyl)-4-hydroxymethyl-oxazol-2-yl]-piperidine-1-carboxylic acid benzyl ester

HRID 2288971Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2288971
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[O:18][C:19]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=3[F:33])=[C:20]([C:22](OC)=[O:23])[N:21]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.[BH4-].[Li+]>CCOCC>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([C:17]2[O:18][C:19]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=3[F:33])=[C:20]([CH2:22][OH:23])[N:21]=2)[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 544076884-[5-(2,4-Difluoro-phenyl)-4-methoxycarbonyl-oxazol-2-yl]-piperidine-1-carboxylic acid benzyl ester

Produkt 1

HCID 539008614-[5-(2,4-Difluoro-phenyl)-4-hydroxymethyl-oxazol-2-yl]-piperidine-1-carboxylic acid benzyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a 0.5 liter round bottom flask fitted with a condenser, nitrogen inlet, and mechanical stirrer is added 30.25 g, 66.3 mmoles of 4-[5-(2,4-Difluoro-phenyl)-4-methoxycarbonyl-oxazol-2-yl]-piperidine-1-carboxylic acid benzyl ester, and a mixture of methanol and ether (4 mL to 200 mL). Lithium borohydride 2.17 g (0.1 mol) is added in three portions and then the mixture is stirred and heated to reflux for 30 minutes. The reaction is allowed to cool and carefully quenched with 400 mL of 0.5 N hydrochloric acid. The resulting mixture is extracted with 3×200 mL of methylene chloride. The organics are combined, washed with brine, dried over magnesium sulfate and concentrated to a thick residue to yield the title compound.

Aufarbeitung

  1. customTo a 0.5 liter round bottom flask fitted with a condenser, nitrogen inlet, and mechanical stirrer
  2. temperatureheated
  3. temperatureto reflux for 30 minutes
  4. temperatureto cool
  5. customcarefully quenched with 400 mL of 0.5 N hydrochloric acid
  6. extractionThe resulting mixture is extracted with 3×200 mL of methylene chloride
  7. washwashed with brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated to a thick residue

Quellen und Nachweise

ORD-Eintrag
ord-ca369f2f5a21473d8021d2800cd97002
Quelldatensatz
uspto-grants-2000_07
Patentnummer
US06090825

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