Potassium Fluoride → 2-Fluoro-3-(pyrrolidin-1-ylmethyl)phenol

HRID 1159397노트

반응식

HRID 1159397 반응식
[Si]([O:8][C:9]1[C:10]([F:21])=[C:11]([CH:18]=[CH:19][CH:20]=1)[CH2:12][N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)(C(C)(C)C)(C)C.[F-].[K+]>CO>[F:21][C:10]1[C:11]([CH2:12][N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:18][CH:19]=[CH:20][C:9]=1[OH:8]

참가 물질

4

반응물 2

HCID 522689Potassium FluorideHCID 686193431-(3-{[Tert-butyl(dimethyl)silyl]oxy}-2-fluorobenzyl)pyrrolidine

생성물 1

HCID 686193012-Fluoro-3-(pyrrolidin-1-ylmethyl)phenol수율 80%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of intermediate 33, 1-(3-{[tert-butyl(dimethyl)silyl]oxy}-2-fluorobenzyl)pyrrolidine (19 g, 60 mmol) in MeOH (200 mL) was added KF (7.1 g, 120 mmol), and the mixture was stirred at RT for 1 h. The reaction mixture evaporated in vacuo. Water (100 mL) and concentrated HCl were added to attain pH˜6. The organic layer was separated. The aqueous one was extracted with CH2Cl2 (2×100 mL). The organic layers were discarded. The aqueous fraction was alkalized with K2CO3 to pH˜10, the aqueous one was extracted with CHCl3. The organic layer was washed with brine, dried over Na2SO4 and evaporated in vacuo, recrystallized from Et2O/hexane mixture (1:1) to give the title compound (9.3 g, 78%, 48 mmol) as a yellow crystals. LCMS data: 197.1 and 196.1 (M+H)+ (calculated for C11H14FNO 195.24). 1H NMR data (DMSO-d6): 9.63 (s, 1H, OH), 6.87-6.96 (m, 1H, H—Ar), 6.71-6.85 (m, 2H, H—Ar), 3.58 (s, 2H, Ar—CH2); 2.36-2.46 (m, 4H), 1.61-1.72 (m, 4H).

후처리

  1. customThe reaction mixture evaporated in vacuo
  2. additionWater (100 mL) and concentrated HCl were added
  3. customThe organic layer was separated
  4. extractionThe aqueous one was extracted with CH2Cl2 (2×100 mL)
  5. extractionthe aqueous one was extracted with CHCl3
  6. washThe organic layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. customevaporated in vacuo
  9. customrecrystallized from Et2O/hexane mixture (1:1)

출처 및 근거

ORD 기록
ord-c1acc92669294f71aec307874443fd09
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812040B2

반응 노트

불러오는 중…