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

HRID 397698ノート

反応式

HRID 397698 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f6eb4d3b2867479d987e7de9e1076811
出典データセット
uspto-grants-2003_08
特許番号
US06610707B1

反応ノート

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