Benzyl Bromide → HCID 59352129、化合物

HRID 2385518ノート

反応式

HRID 2385518 の反応式
[OH:1][C@@H:2]([CH3:25])[CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]2([CH2:16][O:15][C:14]3[CH:17]=[C:18]4[C:22](=[CH:23][C:13]2=3)[CH2:21][CH2:20][O:19]4)[C:5]1=[O:24].[H-].[Na+].[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>O1CCCC1>[CH2:28]([O:1][C@@H:2]([CH3:25])[CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]2([CH2:16][O:15][C:14]3[CH:17]=[C:18]4[C:22](=[CH:23][C:13]2=3)[CH2:21][CH2:20][O:19]4)[C:5]1=[O:24])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 59352450HCID 59352450、化合物

生成物 1

HCID 59352129HCID 59352129、化合物収率 83.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of 1′-[(2S)-2-hydroxypropyl]-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2′(1′H)-one (0.19 mg, 0.56 mmol) in anhydrous tetrahydrofuran (10 mL) was added sodium hydride (60% dispersion in mineral oil, 0.03 g, 0.71 mmol). The solution was stirred at ambient temperature for 30 min, then benzylbromide (0.14 g, 0.84 mmol) was added. The reaction mixture was stirred for 16 h. The solution was cooled to ambient temperature, filtered and concentrated in vacuo to dryness. The residue was purified by flash chromatography with ethyl acetate in hexanes (25%) to afford 1′-[(2S)-2-(benzyloxy)propyl]-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2′(1′H)-one (0.20 g, 77%) as a colorless solid: mp 45-47° C.; 1H NMR (300 MHz, CDCl3) (diastereomers) δ7.30-6.97 (m, 9H), 6.38 (s, 1H), 6.33 (d, J=36.0 Hz, 1H), 4.84 (dd, J=21.7, 8.9 Hz, 1H), 4.68-4.55 (m, 2H), 4.49 (dt, J=8.6, 0.8 Hz, 2H), 4.40 (dd, J=12.0, 3.8 Hz, 1H), 4.01-3.83 (m, 2H), 3.80-3.68 (m, 1H), 2.88 (t, J=8.6 Hz, 3H); 13C NMR (75 MHz, CDCl3) (diastereomers) δ178.1 (2), 161.7 (2), 161.3 (2), 143.0 (2), 138.3 (2), 132.7, 128.6, 128.3 (2), 127.5 (2), 127.3, 123.6 (2), 123.2, 120.3 (2), 119.8 (2), 118.9 (2), 109.7 (2), 93.2, 80.7 (2), 73.2, 72.8, 72.4, 70.9, 70.7, 57.6, 46.1 (2), 29.0 (2), 17.7 (2); MS (ES+) m/z 428.0 (M+23).

後処理

  1. stirringThe reaction mixture was stirred for 16 h
  2. temperatureThe solution was cooled to ambient temperature
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo to dryness
  5. customThe residue was purified by flash chromatography with ethyl acetate in hexanes (25%)

出典と根拠

ORDレコード
ord-33343f5700264e4bb85a769e9f59d663
出典データセット
uspto-grants-2012_09
特許番号
US08263606B2

反応ノート

読み込み中…