Acetic Acid → 2-[2-(4-Fluorophenyl)acetyl]4-morpholin-4-yl-pyrazolidine-1-carboxylic acid benzyl ester

HRID 1061607

Reaktionsgleichung

Reaktionsgleichung von HRID 1061607
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C:14](=O)[CH2:13][N:12]1[C:17](=[O:26])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O.Cl>C1COCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH:14]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[CH2:13][N:12]1[C:17](=[O:26])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 5

HCID 176Acetic AcidHCID 313Hydrochloric Acid2×HCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 129701552-[2-(4-Fluorophenyl)acetyl]-4-oxo-pyrazolidine-1-carboxylic acid benzyl ester

Produkt 1

HCID 207247462-[2-(4-Fluorophenyl)acetyl]4-morpholin-4-yl-pyrazolidine-1-carboxylic acid benzyl esterAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-[2-(4-fluorophenyl)acetyl]-4-oxo-pyrazolidine-1-carboxylic acid benzyl ester, 11, (0.14 g, 0.4 mmol) and morpholine (0.038 mL, 0.43 mmol) in THF at room temperature is added Na(OAc)3BH (0.125 g, 0.6 mmol) and HOAc (0.022 mL, 0.4 mmol). The solution is stirred 12 hours then partitioned between diethyl ether and NaHCO3. The aqueous layer was extracted several times with ether and the organic layers combined, dried, and concentrated in vacuo to a clear oil which was re-dissolved in ether and one equivalent of ethereal HCl is added and a white solid forms. The solid is collected by filtration and 100 mg (60% yield) of the desired product is isolated as the HCl salt.

Aufarbeitung

  1. customthen partitioned between diethyl ether and NaHCO3
  2. extractionThe aqueous layer was extracted several times with ether
  3. customdried
  4. concentrationconcentrated in vacuo to a clear oil which
  5. dissolutionwas re-dissolved in ether
  6. filtrationThe solid is collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-379c0f1ca8c74adab82ec9ea0a8c335c
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06960593B2

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