Cornforth reagent → (S)-1-(2-thiopheneacetyl)-3-piperidinecarboxaldehyde

HRID 432828ノート

反応式

HRID 432828 の反応式
C([C@H:3]1[CH:8]([CH2:9][OH:10])[CH2:7][CH2:6][CH2:5][N:4]1[C:11](=[O:18])[CH2:12][C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)C.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>ClCCl>[S:14]1[CH:15]=[CH:16][CH:17]=[C:13]1[CH2:12][C:11]([N:4]1[CH2:5][CH2:6][CH2:7][C@H:8]([CH:9]=[O:10])[CH2:3]1)=[O:18]

参加物

4

反応物 2

HCID 2724130Cornforth reagentHCID 86759306(S)-ethyl 1-(2-thiopheneacetyl)-3-hydroxymethylpiperidine

生成物 1

HCID 28271707(S)-1-(2-thiopheneacetyl)-3-piperidinecarboxaldehyde収率 32.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(S)-ethyl 1-(2-thiopheneacetyl)-3-hydroxymethylpiperidine (180.4 ml; 0.75 mmol) was dissolved in dichloromethane (20 ml). Crushed molecular sieves (0.25 g), and commercially available pyridinium dichromate (331.2 mg; 0.88 mmol) were added and the mixture was allowed to stir at ambient temperature for 5 hours. The mixture was then filtered through celite, washed with decolorizing carbon, filtered again and then evaporated under reduced pressure at ambient temperature. Crude product was purified by distillation at approximately 250° C./0.1 torr, giving (S)-1-(2-thiopheneacetyl)-3-piperidinecarboxaldehyde (58 mg) as a thick colorless oil. MS m/z (positive ion) 317 (25), 238 (MH+; 100).

後処理

  1. additionwere added
  2. filtrationThe mixture was then filtered through celite
  3. washwashed with decolorizing carbon
  4. filtrationfiltered again
  5. customevaporated under reduced pressure at ambient temperature
  6. distillationCrude product was purified by distillation at approximately 250° C./0.1 torr

出典と根拠

ORDレコード
ord-371169213b284b818385f33124448ed9
出典データセット
uspto-grants-2003_12
特許番号
US06664271B1

反応ノート

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