Aluminium lithium hydride → (2'-Fluoro-2-(2-methylcyclopentyl)-5'-(methyloxy)-1,1'-biphenyl-4-yl)methanol

HRID 1662456노트

반응식

HRID 1662456 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16](OC)=[O:17])=[CH:12][C:11]=1[CH:20]1[CH2:24][CH2:23][CH2:22][CH:21]1[CH3:25].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][OH:17])=[CH:12][C:11]=1[CH:20]1[CH2:24][CH2:23][CH2:22][CH:21]1[CH3:25]

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 57706176Methyl 2'-fluoro-2-(2-methylcyclopentyl)-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate

생성물 1

HCID 57706147(2'-Fluoro-2-(2-methylcyclopentyl)-5'-(methyloxy)-1,1'-biphenyl-4-yl)methanol수율 95%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A 200 mL round bottom flask was charged with 66.56G (0.31 g, 0.91 mmol) and THF (10 mL). To the solution was added LAH (1.0 M in THF) (0.91 mL, 0.91 mmol) dropwise at room temperature. The resulting solution was stirred for 15 minutes, quenched with saturated aqueous Rochelle salt, and extracted with ether. The combined organic layers were dried (MgSO4) and concentrated. The initial product was purified by silica gel flash chromatography (0-30% EtOAc/hexane) to afford 66.56H (mixture of diastereomers) (0.27 g, 95% yield) as a colorless oil.

후처리

  1. customquenched with saturated aqueous Rochelle salt
  2. extractionextracted with ether
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated
  5. customThe initial product was purified by silica gel flash chromatography (0-30% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-07e149b26d594e878df1c5bd5b440cdd
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030354B2

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