Ethoxytrimethylsilane → tert-Butyl 4-methylene-1-oxa-9-azaspiro[5.5]undecane-9-carboxylate

HRID 2040857

반응식

HRID 2040857 반응식
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(O[Si](C)(C)C)C.FC(S(O[Si](C)(C)C)(=O)=O)(F)F.C[Si](C)(C)[CH2:36][C:37](=[CH2:45])[CH2:38][CH2:39][O:40][Si](C)(C)C>C(Cl)(Cl)(Cl)Cl>[CH2:36]=[C:37]1[CH2:45][C:11]2([CH2:12][CH2:13][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9][CH2:10]2)[O:40][CH2:39][CH2:38]1

참가 물질

6

반응물 4

HCID 15772EthoxytrimethylsilaneHCID 65367Trimethylsilyl triflateHCID 7577838tert-Butyl 2-oxopiperidine-1-carboxylateHCID 11806490Trimethyl-(2-methylene-4-trimethylsilyloxybutyl)silane

생성물 1

HCID 57493826tert-Butyl 4-methylene-1-oxa-9-azaspiro[5.5]undecane-9-carboxylate수율 1,000%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매2회

반응 조건

온도
2.5 °C

실험 절차

To a solution of 1-Boc-piperidone (2.39 g, 12 mmol) and ethoxytrimethylsilane (3.75 mL, 24 mmol) in 80 mL of CCl4 under stirring at 0° C. was added trimethylsilyl trifluoromethylsulfonate (217 μL, 1.2 mmol) and trimethyl-(2-methylene-4-trimethylsilyloxybutyl)silane (E. I. Marko et al., Journal of Organic Chemistry 1992, 57, 2211-2213) dissolved in in 23 mL of CCl4. After stirring at 0-5° C. for 6 h and overnight resting at 0° C., the reaction mixture was washed with water, dried on Na2SO4, filtered and the solvent was evaporated to dryness in vacuo. The residual 6.5 g of colourless oil was purified by means of automated flash chromatography (SP1®TM-Biotage; Petroleum Ether-EtOAc gradient from 99:1 to 85:15) to give 3.2 g of the title compound as colourless oil. Yield: 1000%

후처리

  1. customresting at 0° C.
  2. washthe reaction mixture was washed with water
  3. customdried on Na2SO4
  4. filtrationfiltered
  5. customthe solvent was evaporated to dryness in vacuo
  6. customThe residual 6.5 g of colourless oil was purified by means of automated flash chromatography (SP1®TM-Biotage; Petroleum Ether-EtOAc gradient from 99:1 to 85:15)

출처 및 근거

ORD 기록
ord-046ce2b90beb415ebff87294528d8365
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08580962B2

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