Formaldehyde → (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)-4-(4-hydroxy-2-butynyl)piperazine

HRID 584208ノート

反応式

HRID 584208 の反応式
C=O.[F:3][C:4]([F:33])([F:32])[C:5]1[CH:6]=[C:7]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[C:8]([N:10]1[CH2:15][CH2:14][NH:13][CH2:12][C@H:11]1[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[C:19]([CH3:24])[CH:18]=1)=[O:9].[CH2:34]([OH:37])[C:35]#[CH:36].[I-].[K+].[C:40](=O)([O-])O.[Na+]>O1CCOCC1.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[F:33][C:4]([F:3])([F:32])[C:5]1[CH:6]=[C:7]([CH:25]=[C:26]([C:28]([F:29])([F:30])[F:31])[CH:27]=1)[C:8]([N:10]1[CH2:15][CH2:14][N:13]([CH2:40][C:36]#[C:35][CH2:34][OH:37])[CH2:12][C@H:11]1[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[C:19]([CH3:24])[CH:18]=1)=[O:9]

参加物

8

反応物 5

HCID 712FormaldehydeHCID 4875Potassium IodideHCID 7859Propargyl alcoholHCID 516892Sodium BicarbonateHCID 54478438(2R)-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)piperazine

生成物 1

HCID 86588520(2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)-4-(4-hydroxy-2-butynyl)piperazine

試薬・触媒・溶媒 2

HCID 24463Copper sulfate pentahydrate触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A mixture of 37% aqueous formaldehyde (0.21 g), (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)piperazine (0.75.g), propargyl alcohol (0.11 ml), copper(II) sulfate pentahydrate (1.3 mg) and potassium iodide (2.8 mg) in 1,4-dioxane was stirred at 100° C. for 2 hours. After being cooled to room temperature, the mixture was made basic with aqueous saturated sodium hydrogen carbonate solution. The resulting mixture was filtered and the filtrate was extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixed solvent of n-hexane and ethyl acetate (4:1). The fractions containing the objective compound was collected and evaporated under reduced pressure to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)-4-(4-hydroxy-2-butynyl)piperazine (0.78 g) as a syrup.

後処理

  1. temperatureAfter being cooled to room temperature
  2. filtrationThe resulting mixture was filtered
  3. extractionthe filtrate was extracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel using a mixed solvent of n-hexane and ethyl acetate (4:1)
  8. additionThe fractions containing the objective compound
  9. customwas collected
  10. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-53559e9e13004f18822b7469771586da
出典データセット
uspto-grants-2005_08
特許番号
US06924278B2

反応ノート

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