N-bromobutanimide → HCID 59807078、化合物

HRID 1922521ノート

反応式

HRID 1922521 の反応式
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([N:11]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH2:14][CH2:13][CH2:12]3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[Br:21]N1C(=O)CCC1=O>CN(C=O)C.O>[Br:21][C:17]1[CH:16]=[C:15]2[C:20](=[CH:19][CH:18]=1)[N:11]([CH:8]1[CH2:7][CH2:6][C:5]3([O:4][CH2:3][CH2:2][O:1]3)[CH2:10][CH2:9]1)[CH2:12][CH2:13][CH2:14]2

参加物

5

反応物 2

HCID 67184N-bromobutanimideHCID 598070451-(1,4-Dioxaspiro[4.5]decan-8-yl)-1,2,3,4-tetrahydroquinoline

生成物 1

HCID 59807078HCID 59807078、化合物収率 92%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

A solution of compound 3 (0.19 g, 0.695 mmol) in dry DMF (3 mL) was treated with N-bromosuccinimide (0.124 g, 0.695 mmol) in DMF (2 mL) at 0° C. over a period of 10 minutes. The reaction was stirred at the same temperature for 3.5 h. The reaction was diluted with water (50 mL) and the product was extracted into ethyl acetate (2×20 mL). The combined ethyl acetate layer was washed with water (2×20 mL), brine (15 mL) and dried (Na2SO4). Solvent was evaporated and the crude mixture was purified by column chromatography on silica gel (ethyl acetate:hexanes, 1:9) to obtain compound 4 (0.225 g, 92%) as a syrup. 1H NMR (CDCl3) δ 7.16-7.05 (m, 2H), 6.60-6.52 (m, 1H), 3.96 (s, 4H), 3.64-3.55 (m, 1H), 3.20 (t, 2H, J=5.7 Hz), 2.69 (t, 2H, J=6.0 Hz), 1.91-1.54 (m, 10H); ESI-MS (m/z, %): 352, 354 (MH+, 100).

後処理

  1. extractionthe product was extracted into ethyl acetate (2×20 mL)
  2. washThe combined ethyl acetate layer was washed with water (2×20 mL), brine (15 mL)
  3. dry with materialdried (Na2SO4)
  4. customSolvent was evaporated
  5. customthe crude mixture was purified by column chromatography on silica gel (ethyl acetate:hexanes, 1:9)

出典と根拠

ORDレコード
ord-603cfcf43bdf4079b528e75c7c48a2e0
出典データセット
uspto-grants-2012_05
特許番号
US08173813B2

反応ノート

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