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Imidazole → (3aR,4S,5R,6aS)-4-(((tert-Butyldimethylsilyl)oxy)methyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate

HRID 371445
ノート
印刷プレビュー

反応式

HRID 371445 の反応式
[OH:1][CH2:2][C@H:3]1[C@H:10]([O:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:9][C@H:8]2[C@@H:4]1[CH2:5][C:6](=[O:20])[O:7]2.N1C=CN=C1.[Si:26](Cl)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]>CN(C)C=O>[Si:26]([O:1][CH2:2][C@H:3]1[C@H:10]([O:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:9][C@H:8]2[C@@H:4]1[CH2:5][C:6](=[O:20])[O:7]2)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 2724454(3aR,4S,5R,6aS)-5-(Benzoyloxy)hexahydro-4-(hydroxymethyl)-2H-cyclopenta[b]furan-2-one

生成物 1

HCID 2724503(3aR,4S,5R,6aS)-4-(((tert-Butyldimethylsilyl)oxy)methyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate収率 97.9%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

A solution of 11.052 g of (1S,5R,6S,7R)-6-hydroxymethyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one (DOS No. 2,610,718) in 54.0 ml of absolute dimethylformamide is combined with 3.03 g of imidazole and 6.63 g of tert-butyldimethylsilyl chloride, and the mixture is stirred for 3 hours at room temperature. The solution is subsequently precipitated into 500 ml of ice water, the precipitate is suctioned off, and the residue is dissolved in methylene chloride. The organic solution is dried over magnesium sulfate and concentrated. The crude product is recrystallized from hexane, thus obtaining 15.30 g of the title compound, mp 75.8° C.

後処理

  1. customThe solution is subsequently precipitated into 500 ml of ice water
  2. dissolutionthe residue is dissolved in methylene chloride
  3. dry with materialThe organic solution is dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe crude product is recrystallized from hexane

出典と根拠

ORDレコード
ord-cf8b1d4b715f41c8a02044bb836df9bf
出典データセット
uspto-grants-1985_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04532236

反応ノート

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