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Aluminium lithium hydride → 4-[2-Hydroxy-1-(3-trifluoromethyl-phenyl)-ethyl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 550842
ノート
印刷プレビュー

反応式

HRID 550842 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:25](OCC)=[O:26])[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:23])([F:24])[F:22])[CH:16]=2)[CH2:25][OH:26])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 671519624-[Ethoxycarbonyl-(3-trifluoromethyl-phenyl)-methyl]-piperazine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 590119734-[2-Hydroxy-1-(3-trifluoromethyl-phenyl)-ethyl]-piperazine-1-carboxylic acid tert-butyl ester収率 74%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A solution of 4-[Ethoxycarbonyl-(3-trifluoromethyl-phenyl)-methyl]-piperazine-1-carboxylic acid tert-butyl ester (2.10 g, 5.05 mmol) in tetrahydrofuran (30 mL) at 0° C. was added lithium aluminum hydride (1M in tetrahydrofuran, 7.57 mL, 7.57 mmol) dropwise. The mixture was stirred at 0° C. for two hours. The excess LAH was quenched with ethyl acetate and the mixture was stirred with sodium sulfate decahydrate for 10 minutes. The slurry was filtered and the filtrate partitioned between ethyl acetate and water. The organic layer was dried with magnesium sulfate. Filtration, concentration gave a crude which was loaded onto a column of silica gel. Elution with 40% ethyl acetate/hexanes gave 4-[2-Hydroxy-1-(3-trifluoromethyl-phenyl)-ethyl]-piperazine-1-carboxylic acid tert-butyl ester (1.4 g, 74% yield) as a colorless oil. The NMR spectrum obtained on the sample is compatible with its structure.

後処理

  1. customThe excess LAH was quenched with ethyl acetate
  2. stirringthe mixture was stirred with sodium sulfate decahydrate for 10 minutes
  3. filtrationThe slurry was filtered
  4. customthe filtrate partitioned between ethyl acetate and water
  5. dry with materialThe organic layer was dried with magnesium sulfate
  6. filtrationFiltration, concentration
  7. customgave a crude which
  8. washElution with 40% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-24034ec217a94d14aacaea9678800e8f
出典データセット
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07947692B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート