Sodium periodate → 1-Tert-butyl 4-methyl 4-(2-oxopropyl)piperidine-1,4-dicarboxylate

HRID 1501755노트

반응식

HRID 1501755 반응식
[CH3:1][C:2](=C)[CH2:3][C:4]1([C:17]([O:19][CH3:20])=[O:18])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.I([O-])(=O)(=O)=[O:23].[Na+]>O1CCOCC1.O.ClCCl.[Os](=O)(=O)(=O)=O>[O:23]=[C:2]([CH3:1])[CH2:3][C:4]1([C:17]([O:19][CH3:20])=[O:18])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1

참가 물질

6

반응물 2

HCID 23667635Sodium periodateHCID 867094431-tert-Butyl 4-methyl 4-(2-methylallyl)piperidine-1,4-dicarboxylate

생성물 1

HCID 867094441-Tert-butyl 4-methyl 4-(2-oxopropyl)piperidine-1,4-dicarboxylate

시약·촉매·용매 3

HCID 30318Osmium Tetroxide촉매HCID 6344Dichloromethane용매HCID 218864351,4-Dioxane--water (1/1)용매

실험 절차

To a solution of 1-tert-butyl 4-methyl 4-(2-methylallyl)piperidine-1,4-dicarboxylate (2.2 g, 7.4 mmol) in dioxane/water (60 mL, 1/1) under nitrogen was added osmium tetroxide (0.038 g, 0.15 mmol) and sodium periodate (2.88 g, 13.5 mmol). The mixture was stirred at room temperature for 3 hours. The mixture was then diluted with dichloromethane (50 mL), and washed with 20% Na2S2O3 (20 mL). The organic layers were combined and washed with brine (20 mL), dried over anhydrous sodium sulfate, and filtered. The filtrates were concentrated and the residue was purified by column chromatography eluting with 0-60% ethyl acetatehexane to afford 1-tert-butyl 4-methyl 4-(2-oxopropyl)piperidine-1,4-dicarboxylate. LC-MS (IE, m/z): 322.26 (M+23)+.

후처리

  1. washwashed with 20% Na2S2O3 (20 mL)
  2. washwashed with brine (20 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrates were concentrated
  6. customthe residue was purified by column chromatography
  7. washeluting with 0-60% ethyl acetatehexane

출처 및 근거

ORD 기록
ord-be3f3bc26003456e96ec4c9f653fb4ab
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206198B2

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