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Methyl iodide → Tert-butyl 2-methyl-1-oxo-4-phenyl-2,8-diazaspiro[4.6]undecane-8-carboxylate

HRID 1036707
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HRID 1036707 반응식
[O:1]=[C:2]1[C:6]2([CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8][CH2:7]2)[CH:5]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:4][NH:3]1.[Li+].[CH3:27][Si]([N-][Si](C)(C)C)(C)C.IC>C1COCC1>[CH3:27][N:3]1[CH2:4][CH:5]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:6]2([CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:18])([CH3:19])[CH3:17])=[O:14])[CH2:8][CH2:7]2)[C:2]1=[O:1]
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5

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HCID 6328Methyl iodideHCID 2733832Lithium HexamethyldisilazideHCID 71060671Tert-butyl 1-oxo-4-phenyl-2,8-diazaspiro[4.6]undecane-8-carboxylate

생성물 1

HCID 71060314Tert-butyl 2-methyl-1-oxo-4-phenyl-2,8-diazaspiro[4.6]undecane-8-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

A diastereomeric mixture. of tert-butyl 1-oxo-4-phenyl-2,8-diazaspiro[4.6]undecane-8-carboxylate (step 4) (669.5 mg; 1.944 mmol) in THF (19.5 ml) under nitrogen was cooled in an ice/brine bath. 1M LHMDS (2.5 ml, 2.53 mmol) was added and the mixture was stirred at 0° C. for 40 minutes. Iodomethane (182 ul, 2.92 mmol) was added and the mixture was allowed to warm slowly to RT overnight. The reaction was quenched with saturated ammonium chloride solution and extracted with EtOAc. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. Purification by chromatography on silica eluting with EtOAc afforded the title compound;

후처리

  1. temperatureto warm slowly to RT overnight
  2. customThe reaction was quenched with saturated ammonium chloride solution
  3. extractionextracted with EtOAc
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customPurification by chromatography on silica eluting with EtOAc

출처 및 근거

ORD 기록
ord-0d34bff90dd24ab1b48433a9faf67dd4
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08546416B2

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