Pyridine → tert-butyl (2S)-2-(5-[4-(hydroxymethyl)phenoxymethyl]-1,2,4-oxadiazol-3-yl)-1-piperidinecarboxylate

HRID 397649ノート

反応式

HRID 397649 の反応式
N[C@@:2]1(/[CH:15]=[N:16]\[O:17][C:18](=O)[CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([CH2:27][OH:28])=[CH:23][CH:22]=2)[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[N:30]1C=CC=CC=1>>[OH:28][CH2:27][C:24]1[CH:25]=[CH:26][C:21]([O:20][CH2:19][C:18]2[O:17][N:16]=[C:15]([C@@H:2]3[CH2:7][CH2:6][CH2:5][CH2:4][N:3]3[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[N:30]=2)=[CH:22][CH:23]=1

参加物

3

反応物 2

HCID 1049PyridineHCID 140460767tert-butyl (2S)-2-amino-2-[(Z)-[2-[4-(hydroxymethyl)phenoxy]acetyl]oxyiminomethyl]piperidine-1-carboxylate

生成物 1

HCID 57274150tert-butyl (2S)-2-(5-[4-(hydroxymethyl)phenoxymethyl]-1,2,4-oxadiazol-3-yl)-1-piperidinecarboxylate

実験手順

tert-Butyl (Z)-(2S)-2-amino[(2-[4-(hydroxymethyl)phenoxy]acetyloxy)imino]methyl-1-piperidinecarboxylate (see Preparation 12] (2.94 g) was dissolved in pyridine (30 ml) and heated under reflux for 18 hours. The reaction mixture was cooled and the solvent removed under reduced pressure. The residue was partitioned between ethyl acetate and water, the organic layer was separated, dried over magnesium sulphate and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 50:50 changing to 0:100 (in 10% increments), by volume, hexane:ethyl acetate to afford tert-butyl (2S)-2-(5-[4-(hydroxymethyl)phenoxymethyl]-1,2,4-oxadiazol-3-yl)-1-piperidinecarboxylate (1.06 g).

後処理

  1. customPreparation 12] (2.94 g)
  2. temperatureheated
  3. temperatureunder reflux for 18 hours
  4. temperatureThe reaction mixture was cooled
  5. customthe solvent removed under reduced pressure
  6. customThe residue was partitioned between ethyl acetate and water
  7. customthe organic layer was separated
  8. dry with materialdried over magnesium sulphate
  9. customthe solvent removed under reduced pressure
  10. customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 50:50 changing to 0:100 (in 10% increments), by volume, hexane

出典と根拠

ORDレコード
ord-263dc112a84d4161b37ca21b86569cfc
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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