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

HRID 2115617ノート

反応式

HRID 2115617 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-44bc6bd231e648dd9a5312b2e3547281
出典データセット
uspto-grants-2008_10
特許番号
US07435833B2

反応ノート

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