Ethyl Acetate → 4-Chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-ol

HRID 44571

반응식

HRID 44571 반응식
C(N([CH2:8][CH3:9])C(C)C)(C)C.[ClH:10].Br[C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1.[C:18](=[O:21])([O-])[O-].[K+].[K+].CCOC(C)=O>C(#N)C>[Cl:10][C:12]1[CH:17]=[CH:16][N:15]=[C:14]2[CH:18]([OH:21])[CH2:8][CH2:9][C:13]=12

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 881004-Bromopyridinium chloride

생성물 1

HCID 569657354-Chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-ol

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A solution of intermediate 11 (0.0031 mol), N,N-diisopropylethylamine (0.0028 mol), 4-bromopyridine hydrochloride (0.0034 mol) in acetonitrile (20 ml) was heated at 65° C. for 6 hours. Potassium carbonate 10% and EtOAc were added. The reaction mixture was extracted, the organic layer was separated, dried over MgSO4, filtered and concentrated. The residue (1.3 g) was purified by column chromatography over silica gel (eluent 95/5/0.5 DCM/MeOH/NH4OH). Two fractions were collected and the solvent was evaporated to give 60 mg of compound 3 and 80 mg of F2. The residue F2 (80 mg) was purified by supercritical fluid chromatography (AMINO column 150×21.2 mmm) eluent: MeOH/CO2 30/70). The pure fractions were collected and the solvent was evaporated, yielding 43 mg of compound 2.

후처리

  1. extractionThe reaction mixture was extracted
  2. customthe organic layer was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue (1.3 g) was purified by column chromatography over silica gel (eluent 95/5/0.5 DCM/MeOH/NH4OH)
  7. customTwo fractions were collected
  8. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-15259eef555f43be9da38e1f1861a416
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541442B2

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