Acetic Acid → Methyl 9-oxobicyclo[3.3.1]nonane-3-carboxylate

HRID 16219노트

반응식

HRID 16219 반응식
[CH3:1][O:2][C:3](=[O:9])[CH:4]([CH2:7]Br)[CH2:5]Br.[C:10]1(N2CCCC2)[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]=1.C(N(CC)CC)C.C(O)(=[O:30])C>CC#N.O>[CH3:1][O:2][C:3]([CH:4]1[CH2:7][CH:11]2[C:10](=[O:30])[CH:15]([CH2:14][CH2:13][CH2:12]2)[CH2:5]1)=[O:9]

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 707681-Pyrrolidino-1-cyclohexeneHCID 140895Methyl 3-bromo-2-(bromomethyl)propanoate

생성물 1

HCID 19245419Methyl 9-oxobicyclo[3.3.1]nonane-3-carboxylate

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

반응 조건

온도
100 °C

실험 절차

3-Bromo-2-bromomethyl-propionic acid methyl ester (30 g, 115 mmol) was added to a stirred solution of freshly distilled 1-cyclohex-1-enyl-pyrrolidine (20.4 mL, 126 mmol) and triethyl amine (35 mL, 252 mmol) in dry CH3CN (400 mL). After the addition, the mixture was heated (100° C.) and stirred for twelve hours before acetic acid (20 mL) and water (100 mL) were added. Then, heating was continued for another three hours. The solvent was evaporated and the residue was partitioned with diethyl ether and water. The organic phase was washed with a NaHCO3 solution until the washes became basic. It was then dried, filtered, and evaporated. The residue was purified over silica gel using 2-30% diethyl ether in hexanes to give the title compound as a clear oil.

후처리

  1. additionAfter the addition
  2. additionwere added
  3. temperatureThen, heating
  4. customThe solvent was evaporated
  5. customthe residue was partitioned with diethyl ether and water
  6. washThe organic phase was washed with a NaHCO3 solution until the washes
  7. customIt was then dried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified over silica gel using 2-30% diethyl ether in hexanes

출처 및 근거

ORD 기록
ord-499dc9a566d3415a9db0ac30f2538769
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737137B2

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