Dimethyl Sulfoxide → tert-Butyl 4-formylpiperidine-1-carboxylate

HRID 23959

반응식

HRID 23959 반응식
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]([N:18]1[CH2:23][CH2:22][CH:21]([CH2:24][OH:25])[CH2:20][CH2:19]1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].C(N(CC)CC)C>ClCCl.O>[C:11]([N:18]1[CH2:23][CH2:22][CH:21]([CH:24]=[O:25])[CH2:20][CH2:19]1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]

참가 물질

7

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

생성물 1

HCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylate수율 91%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

반응 조건

온도
-78 °C

실험 절차

Dimethyl sulfoxide (3.5 mL, 48.7 mmol) was dissolved in dichloromethane (100 mL) and was cooled to −78° C. Oxalyl chloride (3.65 mL, 41.8 mmol) was added. The mixture stirred for 30 min. To this solution was added a solution of 1-Boc-piperidine-4-methanol (7.5 g, 34.8 mmol) in dichloromethane (15 mL), and the mixture stirred for 1 h. Triethylamine (9.7 mL, 69.6 mmol) was added slowly and the mixture stirred at −78° C. for 30 min and warmed to room temperature over the course of 1 h. The mixture was diluted with water and the layers separated. The water layer was extracted with dichloromethane and the organic layers combined, dried (Na2SO4), filtered and concentrated to provide 1-Boc-piperidine-4-carboxaldehyde (6.75 g, 91%) as a yellow oil.

후처리

  1. stirringthe mixture stirred for 1 h
  2. stirringthe mixture stirred at −78° C. for 30 min
  3. temperaturewarmed to room temperature over the course of 1 h
  4. customthe layers separated
  5. extractionThe water layer was extracted with dichloromethane
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-1da033014a0241498a4e97b2f2c16301
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06855715B1

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