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

HRID 397698Notes

Reaction equation

HRID 397698 reaction equation
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

Participants

4

Reactant 2

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

Product 1

HCID 59085893benzyl 4-(3-[(2S)-2-piperidyl]-1,2,4-oxadiazol-5-ylmethoxy)-1-piperidinecarboxylateYield 96.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f6eb4d3b2867479d987e7de9e1076811
Source dataset
uspto-grants-2003_08
Patent number
US06610707B1

Reaction notes

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