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

HRID 550842
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HRID 550842 반응식
[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]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-24034ec217a94d14aacaea9678800e8f
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07947692B2

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