1-Benzyloxycarbonyl-4-hydroxy-4-(4-benzyloxyphenyl)piperidine → 4-(4-Hydroxyphenyl)piperidin-4-ol

HRID 2381131

Reaktionsgleichung

Reaktionsgleichung von HRID 2381131
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2([OH:31])[CH2:20][CH2:19][N:18](C(OCC3C=CC=CC=3)=O)[CH2:17][CH2:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].CO>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2([OH:31])[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]2)=[CH:11][CH:10]=1

Komponenten

4

Edukt 1

HCID 218398431-Benzyloxycarbonyl-4-hydroxy-4-(4-benzyloxyphenyl)piperidine

Produkt 1

HCID 110632814-(4-Hydroxyphenyl)piperidin-4-olAusbeute 66,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

10% Palladium on carbon (3.44 g, 3.23 mmol) was added to benzyl 4-[4-(benzyloxy)phenyl]-4-hydroxypiperidine-1-carboxylate (13.49 g, 32.31 mmol) in MeOH (146 mL). The resulting mixture was stirred at room temperature for 20 hours under an atmosphere of hydrogen. The reaction mixture was filtered and evaporated to afford crude product. The crude material was triturated with DCM (100 mL) and MeOH (50 mL) to give a solid which was collected by filtration and dried under vacuum to give 4-(4-hydroxyphenyl)piperidin-4-ol (4.16 g, 66.6%). The preparation of 4-(4-hydroxyphenyl)piperidin-4-ol is also described in Journal of Medicinal Chemistry (2000), 43(5), 984-994.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. customevaporated
  3. customto afford crude product
  4. customThe crude material was triturated with DCM (100 mL) and MeOH (50 mL)
  5. customto give a solid which
  6. filtrationwas collected by filtration
  7. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-31ad4dc5fd624e4aa1fae8550d955a0f
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08258140B2

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