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

HRID 1848436ノート

反応式

HRID 1848436 の反応式
[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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 30318Osmium Tetroxide触媒HCID 6344Dichloromethane溶媒HCID 218864351,4-Dioxane--water (1/1)溶媒

実験手順

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 acetate/hexane to afford 1-tert-butyl 4-methyl 4-(2-oxopropyl)piperidine-1,4-dicarboxylate. LC-MS (IE, m/z): 322.26 (M+23)+.

後処理

  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 acetate/hexane

出典と根拠

ORDレコード
ord-26c5fd124d5c4401aa671d22ac9ab6e6
出典データセット
uspto-grants-2015_02
特許番号
US08952166B2

反応ノート

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