Hydrochloric Acid → 1-Azabicyclo(3.3.1)nonan-4-one

HRID 2165531ノート

反応式

HRID 2165531 の反応式
CC(C)([O-:4])C.[K+].C(C([N:14]1[CH2:19][CH2:18][CH2:17][CH:16]([CH2:20][CH2:21][C:22](OCC)=O)[CH2:15]1)C)(OCC)=O.Cl>C1(C)C=CC=CC=1>[N:14]12[CH2:15][CH:16]([CH2:17][CH2:18][CH2:19]1)[C:20](=[O:4])[CH2:21][CH2:22]2

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 70373350HCID 70373350、化合物

生成物 1

HCID 4178971-Azabicyclo(3.3.1)nonan-4-one

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

実験手順

Anhydrous potassium t-butoxide (45.8 g) in anhydrous toluene (1.0 dm3) was heated at reflux and 1-carboethoxyethyl-3-carboethoxyethylpiperidine (35.0 g) in toluene (250 ml) was added over 2 hours. Reflux was maintained for a further 4 hours before cooling to room temperature and concentrated hydrochloric acid (300 ml) was added. The mixture was stirred for 1 hour, then the organic layer was separated and extracted with concentrated hydrochloric acid (225 ml×4). The combined acid extracts were heated at reflux for 16 hours, then basified to pH 10 with potassium carbonate and extracted with chlorofeny (300 ml×6). The combined organic extracts were dried (MgSO4) and concentrated in vacuo to an orange semi-solid (9.7 g). This was purified by chromatography (Alumina grade III) by gradient elution in 3-10% methanol in ethyl acetate. The title compound was isolated as light orange semi-solid (3.5 g). δH (360 MHz, CDCl3), 1.55 (1H, m, CHH), 1.7-1.8 (1H, m, CHH), 1.95 (2H, m, CH2), 2.4 (1H, s, CH), 2.55 (2H, m, CH2CO), 3.1-3.4 (6H, m, 3×CH2N); m/z 139 (M+) (100%).

後処理

  1. temperatureat reflux
  2. temperatureReflux
  3. temperaturewas maintained for a further 4 hours
  4. customthe organic layer was separated
  5. extractionextracted with concentrated hydrochloric acid (225 ml×4)
  6. temperatureThe combined acid extracts were heated
  7. temperatureat reflux for 16 hours
  8. extractionextracted with chlorofeny (300 ml×6)
  9. dry with materialThe combined organic extracts were dried (MgSO4)
  10. concentrationconcentrated in vacuo to an orange semi-solid (9.7 g)
  11. customThis was purified by chromatography (Alumina grade III) by gradient elution in 3-10% methanol in ethyl acetate

出典と根拠

ORDレコード
ord-b9031bedc3fb4041b9abe13ecb67c58f
出典データセット
uspto-grants-1990_07
特許番号
US04940703

反応ノート

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