Potassium Permanganate → (3RS,4RS)-[4-(1-tert-butoxycarbonyl-3-naphthalen-2-ylmethoxy-piperidin-4-yl)-phenyl]-acetic acid

HRID 1858638

Reaktionsgleichung

Reaktionsgleichung von HRID 1858638
[Mn]([O-])(=O)(=O)=[O:2].[K+].[OH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH:17]2[O:29][CH2:30][C:31]2[CH:40]=[CH:39][C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH:32]=2)=[CH:12][CH:11]=1>O.C(O)(=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C1C=CC=CC=1>[C:25]([O:24][C:22]([N:19]1[CH2:20][CH2:21][CH:16]([C:13]2[CH:14]=[CH:15][C:10]([CH2:9][C:8]([OH:2])=[O:7])=[CH:11][CH:12]=2)[CH:17]([O:29][CH2:30][C:31]2[CH:40]=[CH:39][C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH:32]=2)[CH2:18]1)=[O:23])([CH3:28])([CH3:26])[CH3:27]

Komponenten

7

Edukt 2

HCID 516875Potassium PermanganateHCID 53946013tert-butyl (3RS,4RS)-4-[4-(2-hydroxy-ethyl)-phenyl)-3-naphthalen-2-ylmethoxy-piperidine-1-carboxylate

Produkt 1

HCID 22128103(3RS,4RS)-[4-(1-tert-butoxycarbonyl-3-naphthalen-2-ylmethoxy-piperidin-4-yl)-phenyl]-acetic acidAusbeute 50,5 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 176Acetic AcidLösungsmittelHCID 241BenzeneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

6.95 g (44 mmol) of powdered potassium permanganate dissolved in a mixture of 100 ml of water and 100 ml of glacial acetic acid as well as 0.73 g (2 mmol) of tetrabutylammonium iodide were added to a solution of 5.0 g (10.83 mmol) of tert-butyl (3RS,4RS)-4-[4-(2-hydroxy-ethyl)-phenyl]-3-naphthalen-2-ylmethoxy-piperidine-1-carboxylate in 500 ml of benzene. The reaction mixture was stirred intensively for 48 hours. For the working-up, the phases were separated. The organic phase was washed with 100 ml of saturated sodium thiosulphate solution. The aqueous phase was decolorized by the addition of saturated sodium thiosulphate solution and subsequently extracted twice with 100 ml of ethyl acetate and 100 ml of methylene chloride each time. The organic phases were combined, dried over sodium sulphate and evaporated under reduced pressure. For purification, the crude material was chromatographed on silica gel using a 9:1 mixture of methylene chloride and methanol as the eluent after the column had previously been prepared with a 90:10:0.1 mixture of methylene chloride, methanol and ammonia. There were obtained 2.6 g (50% of theory) of (3RS,4RS)-[4-(1-tert-butoxycarbonyl-3-naphthalen-2-ylmethoxy-piperidin-4-yl)-phenyl]-acetic acid as a colourless, amorphous solid; MS: 476 (M+H)+.

Aufarbeitung

  1. customthe phases were separated
  2. washThe organic phase was washed with 100 ml of saturated sodium thiosulphate solution
  3. additionThe aqueous phase was decolorized by the addition of saturated sodium thiosulphate solution
  4. extractionsubsequently extracted twice with 100 ml of ethyl acetate and 100 ml of methylene chloride each time
  5. dry with materialdried over sodium sulphate
  6. customevaporated under reduced pressure
  7. customFor purification
  8. customthe crude material was chromatographed on silica gel using
  9. additiona 9:1 mixture of methylene chloride and methanol as the eluent after the column
  10. customhad previously been prepared with a 90:10:0.1 mixture of methylene chloride, methanol and ammonia

Quellen und Nachweise

ORD-Eintrag
ord-af35f4e067ed4ec9a0051be52a295a80
Quelldatensatz
uspto-grants-2000_11
Patentnummer
US06150526

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