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

HRID 1457219노트

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HRID 1457219 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-408b8951bf974325b04a01a5404ac5ea
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05846990

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