Water → 2-[1-[4-(2-Fluorophenoxymethyl)piperidino]ethyl]-3-methoxypyrazine

HRID 914902ノート

反応式

HRID 914902 の反応式
[F:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[O:4][CH2:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.[C:16]([C:19]1[C:24]([O:25][CH3:26])=[N:23][CH:22]=[CH:21][N:20]=1)(=O)[CH3:17].[BH4-].[Na+].O>CO.CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4].C(OCC)(=O)C>[F:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[O:4][CH2:5][CH:6]1[CH2:7][CH2:8][N:9]([CH:16]([C:19]2[C:24]([O:25][CH3:26])=[N:23][CH:22]=[CH:21][N:20]=2)[CH3:17])[CH2:10][CH2:11]1

参加物

8

反応物 4

HCID 962WaterHCID 5398321-(3-Methoxy-2-pyrazinyl)ethanoneHCID 4311764Sodium borohydrideHCID 171780514-[(2-Fluorophenoxy)methyl]piperidine

生成物 1

HCID 222483652-[1-[4-(2-Fluorophenoxymethyl)piperidino]ethyl]-3-methoxypyrazine収率 11%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒HCID 11026Titanium isopropoxide溶媒

実験手順

After dissolving 1.09 g of 4-(2-fluorophenoxymethyl)piperidine in 15 ml of methanol, 1.53 ml of titanium (IV) tetraisopropoxide and 400 mg of 2-acetyl-3-methoxypyrazine [CAS No. 56343-40-9] were added and the mixture was stirred overnight at room temperature. The reaction solution was cooled on ice, 148 mg of sodium borohydride was added and the mixture was stirred for 5 hours at room temperature. Water and ethyl acetate were added to the reaction solution and the mixture was filtered with celite. The filtrate was extracted with ethyl acetate and the extract was washed with saturated brine and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by NH silica gel column chromatography (solvent: n-hexane/ethyl acetate) to obtain the title compound (100 mg, 11% yield).

後処理

  1. addition56343-40-9] were added
  2. additionwas added
  3. stirringthe mixture was stirred for 5 hours at room temperature
  4. filtrationthe mixture was filtered with celite
  5. extractionThe filtrate was extracted with ethyl acetate
  6. washthe extract was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe residue was purified by NH silica gel column chromatography (solvent: n-hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-968ad34de5c7479697573128e6722aa0
出典データセット
uspto-grants-2007_09
特許番号
US07265108B2

反応ノート

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