Trifluoroacetic acid → benzyl 4-(3-[(2S)-2-piperidyl]-1,2,4-oxadiazol-5-ylmethoxy)-1-piperidinecarboxylate

HRID 397698Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 397698
FC(F)(F)C(O)=O.[CH2:8]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([O:24][CH2:25][C:26]2[O:30][N:29]=[C:28]([C@@H:31]3[CH2:36][CH2:35][CH2:34][CH2:33][N:32]3C(OC(C)(C)C)=O)[N:27]=2)[CH2:20][CH2:19]1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>ClCCl>[NH:32]1[CH2:33][CH2:34][CH2:35][CH2:36][C@H:31]1[C:28]1[N:27]=[C:26]([CH2:25][O:24][CH:21]2[CH2:20][CH2:19][N:18]([C:16]([O:15][CH2:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)=[O:17])[CH2:23][CH2:22]2)[O:30][N:29]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 57120376tert-butyl (2S)-2-{5-[(1-[(benzyloxy)carbonyl]-4-piperidyloxy)methyl]-1,2,4-oxadiazol-3-yl}-1-piperidinecarboxylate

Produkt 1

HCID 59085893benzyl 4-(3-[(2S)-2-piperidyl]-1,2,4-oxadiazol-5-ylmethoxy)-1-piperidinecarboxylateAusbeute 96,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Trifluoroacetic acid (25 ml) was added to a solution of tert-butyl (2S)-2-{5-[(1-[(benzyloxy)carbonyl]-4-piperidyloxy)methyl]-1,2,4-oxadiazol-3-yl}-1-piperidinecarboxylate (1.73 g) [see Preparation 94] in dichloromethane (25 ml) at 0° C. The reaction mixture was stirred for 2 hrs at room temperature, after which time the solvent was removed under reduced pressure and the residue partitioned between ethyl acetate and water. The organic layer was separated and washed with 2N aqueous hydrochloric acid and brine, the combined aqueous layers were then neutralised with saturated sodium hydrogen carbonate and the product re-extracted with ethyl acetate. The organic layer was then separated, dried over magnesium sulphate and the solvent removed under reduced pressure to afford benzyl 4-(3-[(2S)-2-piperidyl]-1,2,4-oxadiazol-5-ylmethoxy)-1-piperidinecarboxylate (1.33 g) as a brown oil.

Aufarbeitung

  1. customafter which time the solvent was removed under reduced pressure
  2. customthe residue partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with 2N aqueous hydrochloric acid and brine
  5. extractionthe product re-extracted with ethyl acetate
  6. customThe organic layer was then separated
  7. dry with materialdried over magnesium sulphate
  8. customthe solvent removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f6eb4d3b2867479d987e7de9e1076811
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06610707B1

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