홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Sodium Hydroxide → (5'-(Difluoromethyl)-2-(2,2-dimethylcyclopentyl)-2'-fluoro-1,1'-biphenyl-4-yl)methanol

HRID 1662445
노트
인쇄 미리보기

반응식

HRID 1662445 반응식
[F:1][CH:2]([F:27])[C:3]1[CH:4]=[CH:5][C:6]([F:26])=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15](OC)=[O:16])=[CH:11][C:10]=2[CH:19]2[CH2:23][CH2:22][CH2:21][C:20]2([CH3:25])[CH3:24])[CH:8]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1>[F:27][CH:2]([F:1])[C:3]1[CH:4]=[CH:5][C:6]([F:26])=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11][C:10]=2[CH:19]2[CH2:23][CH2:22][CH2:21][C:20]2([CH3:24])[CH3:25])[CH:8]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57705984Methyl 5'-(difluoromethyl)-2-(2,2-dimethylcyclopentyl)-2'-fluoro-1,1'-biphenyl-4-carboxylate

생성물 1

HCID 57706837(5'-(Difluoromethyl)-2-(2,2-dimethylcyclopentyl)-2'-fluoro-1,1'-biphenyl-4-yl)methanol수율 77.2%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

반응 조건

온도
0 °C

실험 절차

To a cooled solution of 66.51A (0.8631 g, 2.293 mmol) in dry THF (15.4 mL) at 0° C. was added LAH (1.0 M in THF) (4.6 mL, 4.6 mmol) dropwise. Upon complete addition, the reaction was maintained at 0° C. and was monitored by TLC and LCMS. After 45 minutes, 1N NaOH was added to quench the reaction (gas evolution occurred). The resulting solution was extracted three times with EtOAc. After drying over anhydrous magnesium sulfate, filtration, and concentration, the residue was then purified by flash chromatography (SiO2 gel 60, eluted with 0%-100% EtOAc in hexanes). Fractions containing the desired product were combined and concentrated to a colorless oil as 66.51B (617.1 mg, 77% yield). MS ESI (pos.) m/e: 331.0 (M−H2O)+. Chiral separation of 66.51B was accomplished on a Chiracel-OD column (4% IPA in hexane) to provide 66.51C (peak 1) and 66.51D (peak 2). Both enantiomers were used to synthesize example compounds, and both enantiomers gave active compounds.

후처리

  1. additionUpon complete addition
  2. customto quench
  3. customthe reaction (gas evolution occurred)
  4. extractionThe resulting solution was extracted three times with EtOAc
  5. dry with materialAfter drying over anhydrous magnesium sulfate, filtration, and concentration
  6. customthe residue was then purified by flash chromatography (SiO2 gel 60, eluted with 0%-100% EtOAc in hexanes)
  7. additionFractions containing the desired product

출처 및 근거

ORD 기록
ord-df3a9ffbb52243f8b881f169867fd54c
출처 데이터셋
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08030354B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트