Hydroxyamine hydrochloride → tert-butyl 5-(1-aminoethyl)-4-chloro-1H-indole-1-carboxylate

HRID 475308ノート

反応式

HRID 475308 の反応式
C(=[N:14][CH:15]([C:17]1[C:18]([Cl:33])=[C:19]2[C:23](=[CH:24][CH:25]=1)[N:22]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:21]=[CH:20]2)[CH3:16])(C1C=CC=CC=1)C1C=CC=CC=1.Cl.NO>CO>[NH2:14][CH:15]([C:17]1[C:18]([Cl:33])=[C:19]2[C:23](=[CH:24][CH:25]=1)[N:22]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:21]=[CH:20]2)[CH3:16]

参加物

4

反応物 2

HCID 443297Hydroxyamine hydrochlorideHCID 86694759tert-butyl 5-[1-(benzhydrylideneamino)ethyl]-4-chloro-1H-indole-1-carboxylate

生成物 1

HCID 86694760tert-butyl 5-(1-aminoethyl)-4-chloro-1H-indole-1-carboxylate収率 51.3%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
40 °C

実験手順

To a stirred solution of 324 (880.0 mg, 1.92 mmol) in anhydrous MeOH (20 mL) was added hydroxylamine hydrochloride (532.9 mg, 7.70 mmol), and the reaction mixture was stirred at 40° C. under N2 for 16 h. Volatile solvents were removed in vacuo, and the residue was diluted with EtOAc. The organic layer was washed with sat'd. aq. NaHCO3, water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with an EtOAc/heptane gradient (20 to 100% EtOAc), followed a MeOH/EtOAc (+1% TEA) gradient (0 to 80% MeOH) to afford 290 mg (51.3%) of tert-butyl 5-(1-aminoethyl)-4-chloro-1H-indole-1-carboxylate (326) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 7.99 (d, J=8.7 Hz, 1H), 7.73 (d, J=3.7 Hz, 1H), 7.64 (d, J=8.7 Hz, 1H), 6.71 (d, J=3.7 Hz, 1H), 4.49 (d, J=6.6 Hz, 1H), 2.36-1.90 (m, 2H), 1.63 (s, 9H), 1.26 (d, J=6.6 Hz, 3H).

後処理

  1. customVolatile solvents were removed in vacuo
  2. additionthe residue was diluted with EtOAc
  3. washThe organic layer was washed with sat'd
  4. dry with materialaq. NaHCO3, water and brine, dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by SiO2 chromatography
  8. washeluting with an EtOAc/heptane gradient (20 to 100% EtOAc)

出典と根拠

ORDレコード
ord-10e38649ab7d4f74a43cade0285c3a1f
出典データセット
uspto-grants-2014_01
特許番号
US08637537B2

反応ノート

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