Triacetoxyperiodinane → Tert-butyl 4-(3-oxopropyl)piperidine-1-carboxylate

HRID 1749986노트

반응식

HRID 1749986 반응식
[OH:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[O:1]=[CH:2][CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1

참가 물질

4

반응물 2

HCID 159087TriacetoxyperiodinaneHCID 2800739tert-Butyl 4-(3-hydroxypropyl)tetrahydro-1(2h)-pyridinecarboxylate

생성물 1

HCID 10657745Tert-butyl 4-(3-oxopropyl)piperidine-1-carboxylate수율 88.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of tert-butyl 4-(3-hydroxypropyl)piperidine-1-carboxylate (1.00 g, 4.11 mmol) in methylene chloride (20 mL) was cooled to 0° C., and added with the Dess-Martin reagent (2.27 g, 5.34 mmol), and then the mixture was stirred at room temperature for 4 hours. The reaction mixture was filtered, and the filtrate was washed with saturated aqueous sodium hydrogencarbonate, and then further washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, then the solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain tert-butyl 4-(3-oxopropyl)piperidine-1-carboxylate (0.874 g, 88%).

후처리

  1. filtrationThe reaction mixture was filtered
  2. washthe filtrate was washed with saturated aqueous sodium hydrogencarbonate
  3. washfurther washed with saturated brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-8ada52b783d14dfdac81c0773a41f46c
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156827B2

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