Chlorotrimethylsilane → tert-Butyl 4-((trimethylsilyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 339702노트

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HRID 339702 반응식
[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[Si:15](Cl)([CH3:18])([CH3:17])[CH3:16].CCN(CC)CC>CN(C=O)C>[CH3:16][Si:15]([CH3:18])([CH3:17])[O:1][C:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH:7]=1

참가 물질

5

반응물 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

생성물 1

HCID 10778540tert-Butyl 4-((trimethylsilyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
70 °C

실험 절차

To a 1.0 L flask was added tert-butyl 4-oxopiperidine-1-carboxylate (150.0 g, 752.8 mmol), which was dissolved in DMF (400 mL). To this solution was added TMS-Cl (114.7 mL, 903.4 mmol), followed by NEt3 (251.8 mL, 1807 mmol). The resulting heterogeneous mixture was warmed to 70° C. and stirred overnight under a N2 atmosphere. The mixture was cooled to ambient temperature, diluted with hexanes (250 mL) and filtered. The solids were washed with hexanes (4×250 mL). The combined organic phases were washed with a saturated aqueous NaHCO3 (3×250 mL) and brine (3×250 mL), dried over Na2SO4, and concentrated. The crude product was carried on directly to the next step.

후처리

  1. temperatureThe mixture was cooled to ambient temperature
  2. filtrationfiltered
  3. washThe solids were washed with hexanes (4×250 mL)
  4. washThe combined organic phases were washed with a saturated aqueous NaHCO3 (3×250 mL) and brine (3×250 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-9fbbce51ce0b459194c4ca31da27bb95
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895550B2

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