4-Methylmorpholine → Ethyl (+/-)-4-(4-hydroxymethyl-1,3-oxazol-2-yl)-3-phenylbutanoate

HRID 989899Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 989899
[C:1]([C:4]1[N:5]=[C:6]([CH2:9][CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:7][CH:8]=1)(O)=[O:2].CN1CCOCC1.ClC(OCC)=O.[BH4-].[Na+]>C1COCC1.CO>[OH:2][CH2:1][C:4]1[N:5]=[C:6]([CH2:9][CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:7][CH:8]=1

Komponenten

7

Edukt 4

HCID 79724-MethylmorpholineHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 11220404HCID 11220404, Verbindung

Produkt 1

HCID 23389065Ethyl (+/-)-4-(4-hydroxymethyl-1,3-oxazol-2-yl)-3-phenylbutanoateAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of ethyl (±)-4-(4-carboxy-1,3-oxazol-2-yl)-3-phenylbutanoate (500 mg, 1.65 mmole) in dry THF (8 mL) was added 4-methylmorpholine (0.22 mL, 1.99 mmole) then ethyl chloroformate (0.19 mL, 1.99 mmole) at 0° C. After 10 min, NaBH4 (249 mg, 6.59 mmole) was added all at once, then MeOH (8 mL) was added dropwise. After 30 min, the mixture was quenched with H2O (20 mL) and extracted with EtOAc (3×20 mL). The combined organic extracts were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was chromatographed on silica gel (80% EtOAc/hexanes) to give the title compound (371 mg, 78%) as a yellow oil: MS (ES) m/e 290 (M+H)+.

Aufarbeitung

  1. customat 0° C
  2. additionwas added dropwise
  3. waitAfter 30 min
  4. customthe mixture was quenched with H2O (20 mL)
  5. extractionextracted with EtOAc (3×20 mL)
  6. dry with materialThe combined organic extracts were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was chromatographed on silica gel (80% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-a10f23b0051d445689eb613a346e7c68
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06458814B1

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