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Hydrochloric Acid → HCID 21955378, Verbindung

HRID 2213040
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2213040
[BH4-].[Li+].[OH:3][CH2:4][CH2:5][CH2:6][C:7]1([C:20](OCC2C=CC=CC=2)=[O:21])[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1.Cl.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.C1(C)C=CC=CC=1>[OH:21][CH2:20][C:7]1([CH2:6][CH2:5][CH2:4][OH:3])[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:9][CH2:8]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 4148881Lithium borohydrideHCID 69559203HCID 69559203, Verbindung

Produkt 1

HCID 21955378HCID 21955378, VerbindungAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22635083
Tetrahydrofuran toluene
Lösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Lithium borohydride (500 mg, 22.7 mmol) was added to a solution of 1-(1,1-dimethylethyl) 4-phenylmethyl 4-(3-hydroxypropyl)-1,4-piperidinedicarboxylate (Description 136, 1.05 g, 2.79 mmol) in tetrahydrofuran/toluene (50:50, 20 mL). and the mixture was stirred at 60° C. for 4 hours. The mixture was cooled and hydrochloric acid (2M, 10 mL) was added. The mixture was poured into aqueous sodium carbonate (10%, 100 mL) and extracted with ethyl acetate (3×50 mL). The combined organic fractions were dried (Na2SO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with EtOAc/MeOH (100:0 increasing to 95:5) to give the title compound (563 mg, 74%). 1H NMR (400 MHz, CDCl3) δ 3.67 (2H, t, J 7 Hz), 3.48 (2H, s), 3.47–3.40 (2H, m), 3.35–3.25 (2H, m), 1.7 (2H, br s), 1.6–1.3 (8H, m), and 1.44 (9H, s).

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. dry with materialThe combined organic fractions were dried (Na2SO4)
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by flash column chromatography on silica gel
  6. washeluting with EtOAc/MeOH (100:0 increasing to 95:5)

Quellen und Nachweise

ORD-Eintrag
ord-0d1505ab055046c289016d2437e9cf33
Quelldatensatz
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07105507B2

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