Borane;tetrahydrofuran → HCID 15006482、化合物

HRID 600223ノート

反応式

HRID 600223 の反応式
B.O1CCCC1.[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:15]2[CH2:20][N:19]([CH2:21][CH2:22][CH3:23])[C:18](=O)[CH2:17][O:16]2)[CH:12]=[CH:13][CH:14]=1>C1COCC1>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:15]2[O:16][CH2:17][CH2:18][N:19]([CH2:21][CH2:22][CH3:23])[CH2:20]2)[CH:12]=[CH:13][CH:14]=1

参加物

4

反応物 2

HCID 2723981Borane;tetrahydrofuranHCID 150064786-(3-Methoxyphenyl)-4-Propylmorpholin-3-one

生成物 1

HCID 15006482HCID 15006482、化合物収率 84%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Borane-tetrahydrofuran complex (1M in THF) (200 ml, 0.19 mol) was added dropwise to the morpholin-3-one from example 5 (15.8 g, 0.06 mol) in dry THF (10 ml) under an atmosphere of nitrogen, over 30 minutes. The reaction mixture was brought to reflux for 3 hours then cooled and quenched by addition of methanol (S3 ml). The reaction mixture was then concentrated in vacuo and the colourless residue cautiously suspended in 4N HCl (aq) (400 ml) before refluxing for 2.5 hours. The reaction mixture was cooled and dichloromethane (200 ml) added. Layers were separated and the aqueous layer rendered basic by addition of potassium carbonate before re-extracting with dichloromethane (3×100 ml). The organic extracts were combined, dried over anhydrous magnesium sulphate, filtered and concentrated in vacuo to give the title compound as a colourless oil (12.51 g, 0.05 mmol, 84%). 1H NMR (CDCl3, 400 MHz) δ: 0.95 (t, 3H), 1.59 (q, 2H), 2.05 (t, 1H), 2.23 (t, 1H), 2.40 (t, 2H), 2.81 (d, 1H), 2.98 (d, 1H), 3.80 (s, 3H), 3.85 (t, 1H), 4.05 (d, 1H), 4.60 (d, 1H), 6.81 (d, 1H), 6.91 (d, 1H), 7.21 (t, 1H), 7.23 (s 5.1H) LRMS, m/z 236. Analysis found C, 68.94; H, 8.80; N, 5.79%. C14H21NO2.0.5H2O requires C, 68.82; H, 9.08; N, 5.73%.

後処理

  1. temperatureto reflux for 3 hours
  2. temperaturethen cooled
  3. customquenched by addition of methanol (S3 ml)
  4. concentrationThe reaction mixture was then concentrated in vacuo
  5. temperaturebefore refluxing for 2.5 hours
  6. temperatureThe reaction mixture was cooled
  7. additiondichloromethane (200 ml) added
  8. customLayers were separated
  9. additionthe aqueous layer rendered basic by addition of potassium carbonate
  10. extractionbefore re-extracting with dichloromethane (3×100 ml)
  11. dry with materialdried over anhydrous magnesium sulphate
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-deee3068ac2b459fbe179e07492e0eb7
出典データセット
uspto-grants-2011_03
特許番号
US07902188B2

反応ノート

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