Trifluoroacetic acid → HCID 60123707、化合物

HRID 1368068ノート

反応式

HRID 1368068 の反応式
[CH:1]1([C:4](=[O:7])[CH:5]=[CH2:6])[CH2:3][CH2:2]1.C(O[CH2:13][N:14]([CH2:23][Si](C)(C)C)[C@@H:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH3:16])CCC.FC(F)(F)C(O)=O>ClC(Cl)C>[CH:1]1([C:4]([CH:5]2[CH2:6][CH2:13][N:14]([C@@H:15]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH3:16])[CH2:23]2)=[O:7])[CH2:3][CH2:2]1

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 5349541-Cyclopropyl-2-propen-1-oneHCID 15701915HCID 15701915、化合物

生成物 1

HCID 60123707HCID 60123707、化合物収率 49.6%

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

実験手順

The product containing 1-cyclopropyl-2-propen-1-one described in Reference Example 1 (8.01 g) and N-(normal-butoxymethyl)-N-[1-(R)-phenylethyl]trimethylsilylmethylamine (23.2 g, 79.9 mmol) were dissolved in dry dichloroethane (350 ml) to which was subsequently added dropwise trifluoroacetic acid (500 μl). After 12 hours of stirring at room temperature, the reaction solution was washed with saturated sodium bicarbonate aqueous solution (100 ml) and saturated sodium chloride aqueous solution (100 ml) in that order. This was dried over anhydrous magnesium sulfate, filtered and then concentrated under a reduced pressure. The resulting residue was applied to a flash silica gel chromatography and eluted with n-hexane:ethyl acetate=2:1, thereby obtaining 9.08 g (49.6%) of the title compound as a colorless oil. In this connection, this product was obtained as a 1:1 diastereomer mixture.

後処理

  1. washthe reaction solution was washed with saturated sodium bicarbonate aqueous solution (100 ml) and saturated sodium chloride aqueous solution (100 ml) in that order
  2. dry with materialThis was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under a reduced pressure
  5. washeluted with n-hexane

出典と根拠

ORDレコード
ord-73df22791e25463bbcd4edd7f0910b76
出典データセット
uspto-grants-2003_06
特許番号
US06573260B1

反応ノート

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