Water → HCID 15125573, Verbindung

HRID 48477Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 48477
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][C:17]([N:20]4[CH:24]=[N:23][N:22]([CH:25]([CH3:29])[C:26](=[O:28])[CH3:27])[C:21]4=[O:30])=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C([BH-](C(CC)C)C(CC)C)(CC)C.[K+].O>CN(C=O)C.O1CCCC1>[OH:28][CH:26]([CH3:27])[CH:25]([N:22]1[C:21](=[O:30])[N:20]([C:17]2[CH:16]=[CH:15][C:14]([N:11]3[CH2:10][CH2:9][N:8]([C:5]4[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=4)[CH2:13][CH2:12]3)=[CH:19][CH:18]=2)[CH:24]=[N:23]1)[CH3:29]

Komponenten

6

Edukt 3

HCID 962WaterHCID 4304157Potassium;tri(butan-2-yl)boranuideHCID 151255654-{4-[4-(4-Hydroxyphenyl)piperazin-1-yl]phenyl}-2-(3-oxobutan-2-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one

Produkt 1

HCID 15125573HCID 15125573, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

A mixture of (±)-2,4-dihydro-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-2-(1-methyl-2-oxopropyl)-3H-1,2,4-triazol-3-one (0.06 mol) in DMF (500 ml) was cooled to −10° C. and then stirred under N2 flow. Potassium tri-sec-butylborohydride, 1M solution in tetrahydrofuran (150 ml) was added dropwise. The mixture was allowed to warm to room temperature slowly and then poured out into water. The precipitate was filtered off, washed with CH3OH and crystallized from CH3OH. The precipitate was filtered off and dried. The residue was purified by HPLC over CHIRALPAC AD (eluent: ethanol). Two pure fractions were collected and their solvents were evaporated. Each residue was triturated in CH3OH. The precipitate was filtered off and dried, yielding 7.3 g [S—(R*,R*)]-2,4-dihydro-2-(2-hydroxy-1-methylpropyl)-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-3H-1,2,4-triazol-3-one. (interm. 1a) [α]20D=−10.81° (c=50.43 mg/5 ml DMF).

Aufarbeitung

  1. temperatureto warm to room temperature slowly
  2. filtrationThe precipitate was filtered off
  3. washwashed with CH3OH
  4. customcrystallized from CH3OH
  5. filtrationThe precipitate was filtered off
  6. customdried
  7. customThe residue was purified by HPLC over CHIRALPAC AD (eluent: ethanol)
  8. customTwo pure fractions were collected
  9. customtheir solvents were evaporated
  10. customEach residue was triturated in CH3OH
  11. filtrationThe precipitate was filtered off
  12. customdried

Quellen und Nachweise

ORD-Eintrag
ord-06a969b7c3924dfc9cf150d91d039ab1
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06703506B2

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