Iodoethane → 3-(3,4-Difluorophenyl)-1-ethyl-3-methoxypyrrolidine

HRID 1188155ノート

反応式

HRID 1188155 の反応式
[F:1][C:2]1[CH:3]=[C:4]([C:9]2([O:14][CH3:15])[CH2:13][CH2:12][NH:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8].C(=O)([O-])[O-].[K+].[K+].I[CH2:23][CH3:24].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:9]2([O:14][CH3:15])[CH2:13][CH2:12][N:11]([CH2:23][CH3:24])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

参加物

7

反応物 4

HCID 6340IodoethaneHCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 462192213-(3,4-Difluorophenyl)-3-methoxypyrrolidine

生成物 1

HCID 462192223-(3,4-Difluorophenyl)-1-ethyl-3-methoxypyrrolidine収率 46.6%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 3-(3,4-difluorophenyl)-3-methoxypyrrolidine (0.19 g, 0.89 mmol) in acetonitrile (5 ml), potassium carbonate (0.17 g, 1.25 mmol) and iodoethane (0.075 ml, 0.94 mmol) was added and the mixture was stirred at ambient temperature for 5 h. Aqueous sodiumcarbonate (10%, 50 ml) and ethyl acetate (50 ml) was added and the organic phase was collected. The aqueous phase was extracted with ethyl acetate (2×50 ml) and the combined organic phase was washed with Brine, dried (Na2SO4) and evaporated to give the crude product. Purification on a Biotage Isolute SCX-3 SPE column (washed with methanol and eluted with methanol/triethylamine, 4:1) followed by flash column chromatography on silica gel (EtOAc/MeOH 4:1) gave the title compound (0.10 g, 46%). The amine was converted to the oxalic acid salt and recrystallized from methanol/diethyl ether: M.p. 135-136° C. MS m/z (rel. intensity, 70 eV) 241 (4), 226 (27), 211(17), 141 (26), 71 (bp).

後処理

  1. customthe organic phase was collected
  2. extractionThe aqueous phase was extracted with ethyl acetate (2×50 ml)
  3. washthe combined organic phase was washed with Brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customto give the crude product
  7. customPurification
  8. washon a Biotage Isolute SCX-3 SPE column (washed with methanol and eluted with methanol/triethylamine, 4:1)

出典と根拠

ORDレコード
ord-5c34c117cc944187a3aab3075310f21e
出典データセット
uspto-grants-2014_03
特許番号
US08673962B2

反応ノート

読み込み中…