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

HRID 44571

反応式

HRID 44571 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-15259eef555f43be9da38e1f1861a416
出典データセット
uspto-grants-2013_09
特許番号
US08541442B2

関連ノート

読み込み中…