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

HRID 432828노트

반응식

HRID 432828 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(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).

후처리

  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

출처 및 근거

ORD 기록
ord-371169213b284b818385f33124448ed9
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06664271B1

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