Hydrochloric Acid → (2RS,9aSR)-9a-butyl-7-hydroxy-2-(3-hydroxy-2-oxopropyl)4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HRID 7873ノート

反応式

HRID 7873 の反応式
[CH2:1]([C:5]12[CH2:17][CH:16]([CH2:18][C:19](=[O:22])[CH2:20][OH:21])[C:15](=[O:23])[C:14]([CH3:24])=[C:13]1[C:12]1[C:7](=[CH:8][C:9]([O:25]COC)=[CH:10][CH:11]=1)[CH2:6]2)[CH2:2][CH2:3][CH3:4].Cl>CO>[CH2:1]([C:5]12[CH2:17][CH:16]([CH2:18][C:19](=[O:22])[CH2:20][OH:21])[C:15](=[O:23])[C:14]([CH3:24])=[C:13]1[C:12]1[C:7](=[CH:8][C:9]([OH:25])=[CH:10][CH:11]=1)[CH2:6]2)[CH2:2][CH2:3][CH3:4]

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 67398080(2RS,9aSR)-9a-butyl-2-(3-hydroxy-2-oxopropyl)-7-methoxymethoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

生成物 1

HCID 10268956(2RS,9aSR)-9a-butyl-7-hydroxy-2-(3-hydroxy-2-oxopropyl)4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of (2RS,9aSR)-9a-butyl-2-(3-hydroxy-2-oxopropyl)-7-methoxymethoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (24 mg, 0.06 mmol) in methanol (1 mL) was treated with 2N HCl (0.36 mL, 0.18 mmol) and the resulting solution was heated at reflux for 20 minutes. After cooling, the mixture was concentrated under vacuum to a residue that was dissolved in EtOAc (60 mL) and washed with 5% NaHCO3 (30 mL). The aqueous phase was back-extracted with EtOAc (30 mL). The combined organics were washed with brine, dried over MgSO4, filtered, and evaporated under vacuum. The residue was purified by PLC, using 1:1 hexanes-EtOAc as developing solvent, to afford (2RS,9aSR)-9a-butyl-7-hydroxy-2-(3-hydroxy-2-oxopropyl)-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one as an oil.

後処理

  1. temperaturethe resulting solution was heated
  2. temperatureat reflux for 20 minutes
  3. temperatureAfter cooling
  4. concentrationthe mixture was concentrated under vacuum to a residue that
  5. dissolutionwas dissolved in EtOAc (60 mL)
  6. washwashed with 5% NaHCO3 (30 mL)
  7. extractionThe aqueous phase was back-extracted with EtOAc (30 mL)
  8. washThe combined organics were washed with brine
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. customevaporated under vacuum
  12. customThe residue was purified by PLC

出典と根拠

ORDレコード
ord-b15b3e94ee9748ad969eea6cc232a478
出典データセット
uspto-grants-2006_08
特許番号
US07087599B2

反応ノート

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