Tert-butyl 4-(pyridin-4-ylmethyl)piperidine-1-carboxylate → 4-Piperidin-4-ylmethyl-piperidine-1-carboxylic acid t-butyl ester

HRID 1869620Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1869620
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[CH:3][CH:2]=1>C(O)C.C(O)(=O)C.[Pt]=O>[NH:1]1[CH2:2][CH2:3][CH:4]([CH2:7][CH:8]2[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH2:13]2)[CH2:5][CH2:6]1

Komponenten

5

Edukt 1

HCID 18539261Tert-butyl 4-(pyridin-4-ylmethyl)piperidine-1-carboxylate

Produkt 1

HCID 497611974-Piperidin-4-ylmethyl-piperidine-1-carboxylic acid t-butyl esterAusbeute 80,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 82844Platinum oxide (PtO)KatalysatorHCID 176Acetic AcidLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

1,1-Dimethylethyl 4-(4-pyridinylmethyl)-1-piperidinecarboxylate (may be prepared as described in Description 1) (11.4 g) was dissolved in ethanol (200 ml) and acetic acid (2.36 ml). Platinum oxide (2 g) was added under a blanket of argon, and the reaction shaken under hydrogen at 50 psi for 18 h. After carefully filtering off the platinum catalyst, the solvent was evaporated and the residue redissolved in ethyl acetate (50 ml) and washed with saturated sodium hydrogen carbonate solution (50 ml). The aqueous phase was extracted into ethyl acetate (2×50 ml) and the combined organics dried (Na2SO4) and evaporated to give the title compound (D2) as white solid (9.4 g).

Aufarbeitung

  1. filtrationAfter carefully filtering off the platinum catalyst
  2. customthe solvent was evaporated
  3. dissolutionthe residue redissolved in ethyl acetate (50 ml)
  4. washwashed with saturated sodium hydrogen carbonate solution (50 ml)
  5. extractionThe aqueous phase was extracted into ethyl acetate (2×50 ml)
  6. dry with materialthe combined organics dried (Na2SO4)
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-076c84a7209e426891f0bab459b08db4
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07638631B2

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