Acetic Acid → (3aR,4R,5R,6aS)-4-((R)-3-Hydroxy-5-phenylpentyl)hexahydro-2H-cyclopenta[b]furan-2,5-diol

HRID 584886ノート

反応式

HRID 584886 の反応式
[OH:1][C@@H:2]1[CH2:10][C@@H:5]2[O:6][CH:7]([OH:9])[CH2:8][C@@H:4]2[C@H:3]1[CH2:11][CH2:12][C@@H:13]([O:22]C1CCCCO1)[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O)(=O)C.C1COCC1.[OH-].[K+]>O>[OH:1][C@@H:2]1[CH2:10][C@@H:5]2[O:6][CH:7]([OH:9])[CH2:8][C@@H:4]2[C@H:3]1[CH2:11][CH2:12][C@@H:13]([OH:22])[CH2:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 10110977(3aR,4R,5R,6aS)-Hexahydro-5-hydroxy-4-[(3R)-5-phenyl-3-[(tetrahydro-2H-pyran-2-yl)oxy]pentyl]-2H-cyclopenta[b]furan-2-ol

生成物 1

HCID 10425274(3aR,4R,5R,6aS)-4-((R)-3-Hydroxy-5-phenylpentyl)hexahydro-2H-cyclopenta[b]furan-2,5-diol収率 43%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
45 °C

実験手順

A mixture of compound [11a] (0.55 g), acetic acid (2 ml), THF (2 mL) and water (2 mL) was stirred at 40-50° C. for 4 hours (TLC monitoring). The mixture was basified with 1 N aq. potassium hydroxide to pH 10-11 and the product was extracted with dichloromethane (3×20 mL). The combined organic layers were dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (elution with gradient ethyl acetate/hexane from 1:2 to 3:1 v/v) to give 0.18 g (43%) of the compound [11b] as a colorless oil. 1H NMR (CD3OD) is compatible with literature data.

後処理

  1. extractionthe product was extracted with dichloromethane (3×20 mL)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (elution with gradient ethyl acetate/hexane from 1:2 to 3:1 v/v)

出典と根拠

ORDレコード
ord-d06e9afb6d9947949531e0f30b3afa13
出典データセット
uspto-grants-2005_08
特許番号
US06927300B2

反応ノート

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