ethyl [(2R*,6S*)-2-(4-fluorophenyl)-6-vinylpiperidin-1-yl]oxoacetate → (6R*,9aS*)-6-(4-fluorophenyl)-3-hydroxyhexahydropyrido[2,1-c][1,4]oxazin-4-one

HRID 1436091노트

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HRID 1436091 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:13][CH2:12][CH2:11][C@@H:10](C=C)[N:9]2[C:16](=[O:22])[C:17]([O:19][CH2:20]C)=[O:18])=[CH:4][CH:3]=1>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]2[N:9]3[C@H:10]([CH2:20][O:19][CH:17]([OH:18])[C:16]3=[O:22])[CH2:11][CH2:12][CH2:13]2)=[CH:6][CH:7]=1

참가 물질

3

반응물 1

HCID 86612603ethyl [(2R*,6S*)-2-(4-fluorophenyl)-6-vinylpiperidin-1-yl]oxoacetate

생성물 1

HCID 69010340(6R*,9aS*)-6-(4-fluorophenyl)-3-hydroxyhexahydropyrido[2,1-c][1,4]oxazin-4-one수율 13.6%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
-78 °C

실험 절차

A solution of ethyl [(2R*,6S*)-2-(4-fluorophenyl)-6-vinylpiperidin-1-yl]oxoacetate (220 mg) in methanol (5 mL) was cooled to −78° C., and ozone gas was bubbled through the reaction solution for 20 minutes. Sodium borohydride (164 mg) was added to the reaction solution while stirring at −78° C., and the reaction solution was stirred at that temperature for 30 minutes. Ethyl acetate and a saturated ammonium chloride solution were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane:ethyl acetate=1:1->ethyl acetate) to obtain 26 mg of the title compound. The property values of the compound are as follows.

후처리

  1. customozone gas was bubbled through the reaction solution for 20 minutes
  2. additionSodium borohydride (164 mg) was added to the reaction solution
  3. stirringthe reaction solution was stirred at that temperature for 30 minutes
  4. additionEthyl acetate and a saturated ammonium chloride solution were added to the reaction solution
  5. customthe organic layer was separated
  6. dry with materialThe resulting organic layer was dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (elution solvent: heptane:ethyl acetate=1:1->ethyl acetate)

출처 및 근거

ORD 기록
ord-cf8f8280c320409aae249328fcbf6b4a
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07618960B2

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