Borane;tetrahydrofuran → HCID 15006482, 화합물

HRID 2102342노트

반응식

HRID 2102342 반응식
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

참가 물질

4

반응물 2

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

생성물 1

HCID 15006482HCID 15006482, 화합물수율 84%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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 (100 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 (30 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 mol, 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 (d1H), 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, 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%.

후처리

  1. temperatureto reflux for 3 hours
  2. temperaturethen cooled
  3. customquenched by addition of methanol (30 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

출처 및 근거

ORD 기록
ord-1361e083e8b84b7db13fc45d6f5953d5
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07576081B2

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