Citric Acid → 1,1-Dimethylethyl 3,3-dimethyl-2-oxo-1-piperidinecarboxylate

HRID 1457219ノート

反応式

HRID 1457219 の反応式
O=[C:2]1CCCC[N:3]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:25]I.C(O)(=O)[CH2:28][C:29]([CH2:34][C:35](O)=O)([C:31]([OH:33])=O)O>C1COCC1.CCOCC>[CH3:25][C:29]1([CH3:28])[CH2:34][CH2:35][CH2:2][N:3]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C:31]1=[O:33]

参加物

7

反応物 4

HCID 311Citric AcidHCID 6328Methyl iodideHCID 2733832Lithium HexamethyldisilazideHCID 7577838tert-Butyl 2-oxopiperidine-1-carboxylate

生成物 1

HCID 572676081,1-Dimethylethyl 3,3-dimethyl-2-oxo-1-piperidinecarboxylate

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To the title compound of Step (A) (1.08 g, 5.42 mmol) in 10.8 ml THF at -78° C., lithium bis(trimethylsilyl)amide (1M in THF, 13.6 ml, 13.6 mmol) was added dropwise in 10 min. The mixture was stirred at -78° C. for 30 minutes and methyl iodide (4.62 g, 32.52 mmol) was added. The reaction mixture was slowly warmed to room temperature and stirred at room temperature for two days. To the reaction mixture, 30 ml Et2O and 15 ml 5% aqueous citric acid were added. The organic liquid was separated and washed with 10 ml 5% citric acid, H2O, brine and dried and concentrated. The residue was chromatographed on silica gel using 19:1 hexane/EtOAc to give the title compound of this step (440 mg, 38%) as a light yellow oil.

後処理

  1. temperatureThe reaction mixture was slowly warmed to room temperature
  2. stirringstirred at room temperature for two days
  3. customThe organic liquid was separated
  4. washwashed with 10 ml 5% citric acid, H2O, brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel using 19:1 hexane/EtOAc

出典と根拠

ORDレコード
ord-408b8951bf974325b04a01a5404ac5ea
出典データセット
uspto-grants-1998_12
特許番号
US05846990

反応ノート

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