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Sodium triacetoxyborohydride → HCID 178453913, Verbindung

HRID 2265901
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2265901
[N:1]1([C:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[O:9][N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:16]([O:20][C:21](=[O:32])[NH:22][C@H:23]1[CH2:28][CH2:27][C@H:26]([CH2:29][CH:30]=O)[CH2:25][CH2:24]1)([CH3:19])([CH3:18])[CH3:17].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[C:16]([O:20][C:21](=[O:32])[NH:22][C@H:23]1[CH2:24][CH2:25][C@H:26]([CH2:29][CH2:30][N:4]2[CH2:5][CH2:6][N:1]([C:7]3[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=4[O:9][N:8]=3)[CH2:2][CH2:3]2)[CH2:27][CH2:28]1)([CH3:19])([CH3:18])[CH3:17]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 5049666Sodium triacetoxyborohydrideHCID 132324753-(Piperazin-1-yl)-1,2-benzoxazoleHCID 178453924HCID 178453924, Verbindung2×

Produkt 1

HCID 178453913HCID 178453913, VerbindungAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 3-piperazin-1-yl-1,2-benzisoxazole (1 g, 4.92 mmol), trans-[4-(2-oxo-ethyl)-cyclohexyl]-carbamic acid tert-butyl ester (Intermediate A) (1.3 g, 5.41 mmol), in dichloromethane (15 ml) was stirred for 15 minutes at room temperature and sodium triacetoxyborohydride (1.88 g, 8.86 mmol) was added slowly and the resulting solution was stirred for 12 hours until the TLC indicated completion of the reaction. The mixture was extracted with saturated NaHCO3-solution and two times dichloromethane. The organic layers were dried over sodium sulfate, filtrated and concentrated to dryness. The crude product was purified with column chromatography on silica gel using heptane:ethyl acetate 80:20->10:90. The product fractions were concentrated to give 1.34 g (64% yield) of a white solid. MS (m/e): 429.4 (M+H+).

Aufarbeitung

  1. customcompletion of the reaction
  2. extractionThe mixture was extracted with saturated NaHCO3-solution and two times dichloromethane
  3. dry with materialThe organic layers were dried over sodium sulfate
  4. filtrationfiltrated
  5. concentrationconcentrated to dryness
  6. customThe crude product was purified with column chromatography on silica gel
  7. concentrationThe product fractions were concentrated

Quellen und Nachweise

ORD-Eintrag
ord-a0d829c9ae874f3f95723a94f2f17bde
Quelldatensatz
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07858630B2

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