Methyl iodide → 4-[2-Methoxy-1-(3-trifluoromethyl-phenyl)-ethyl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 550843ノート

反応式

HRID 550843 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=2)[CH2:15][OH:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:30]>O1CCCC1.CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:25])([F:26])[F:24])[CH:18]=2)[CH2:15][O:16][CH3:30])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 590119734-[2-Hydroxy-1-(3-trifluoromethyl-phenyl)-ethyl]-piperazine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 590119454-[2-Methoxy-1-(3-trifluoromethyl-phenyl)-ethyl]-piperazine-1-carboxylic acid tert-butyl ester収率 92.3%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A mixture of 4-[2-Hydroxy-1-(3-trifluoromethyl-phenyl)-ethyl]-piperazine-1-carboxylic acid tert-butyl ester (200 mg, 0.53 mmol) in tetrahydrofuran (5 mL) and N,N-dimethylformamide (5 mL) at 0° C. was added sodium hydride (60% in mineral oil, 70 mg, 1.75 mmol) followed by iodomethane (230 mg, 1.62 mmole). The mixture was stirred at 0° C. for three hours. The reaction was quenched with saturated aqueous ammonium chloride solution and partitioned between ethyl acetate and water. The organic layer was dried with magnesium sulfate. Filtration, concentration gave a crude oil which was loaded onto a column of silica gel. Elution with 50% ethyl acetate/hexanes gave 4-[2-Methoxy-1-(3-trifluoromethyl-phenyl)-ethyl]-piperazine-1-carboxylic acid tert-butyl ester (190 mg, 92% yield) as a colorless oil. The NMR spectrum obtained on the sample is compatible with its structure.

後処理

  1. customThe reaction was quenched with saturated aqueous ammonium chloride solution
  2. custompartitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried with magnesium sulfate
  4. filtrationFiltration, concentration
  5. customgave a crude oil which
  6. washElution with 50% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-291393b264c04030b02fbe21f89be22a
出典データセット
uspto-grants-2011_05
特許番号
US07947692B2

反応ノート

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