Hydrochloric Acid → HCID 68882717、化合物

HRID 1269492ノート

反応式

HRID 1269492 の反応式
[CH2:1]([O:3][C:4](=[O:21])[C:5]([CH3:20])([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH:9]=1)[CH3:6])C.Cl.[H][H]>CO.[Pt]>[CH3:1][O:3][C:4](=[O:21])[C:5]([CH3:6])([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]2[CH2:19][CH2:18][CH2:17][NH:16][CH2:15]2)[CH:9]=1)[CH3:20]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 688835012-Methyl-2-(3-pyridin-3-yl-phenoxy)-propionic acid ethyl esterHCID 178418361HCID 178418361、化合物

生成物 1

HCID 68882717HCID 68882717、化合物収率 82.3%

試薬・触媒・溶媒 2

HCID 23939Platinum触媒HCID 887Methanol溶媒

実験手順

2-methyl-2-(3-pyridin-3-yl-phenoxy)-propionic acid ethyl ester (6.0 g, 21.03 mmol) was dissolved in methanol (70 mL) and followed by the addition of 37% HCl (5.3 mL) and 10% Pt/C (0.60 g). The mixture was shaken with hydrogen under 50 psi at 50° C. in a Parr bottle for 5 h, filtered through a pad of Celite, and rinsed with methanol. GC/MS showed complete hydrogenation and only 50% of methyl ester conversion. Concentrated H2SO4 (2.0 mL) was added to the filtrate and the resulting solution was allowed to reflux under nitrogen overnight. After removal of excess methanol, the residue was treated with saturated Na2CO3 (150 mL) and extracted with ethyl acetate (2×200 mL). The organic extract was washed with water, dried over sodium sulfate, and concentrated to give 4.80 g (82%) of 2-methyl-2-(3-piperidin-3-yl-phenoxy)-propionic acid methyl ester as a yellow oil: 1H NMR (CDCl3) δ 1.59 (s, 6H), 1.78 (br, 1H), 1.97 (br d, 1H), 2.02 (br, 2H), 2.61 (m, 3H), 3.06 –3.13 (m, 2H), 3.76 (s, 3H), 6.61 (dd, 1H), 6.70 (s, 1H), 6.83 (d, 1H), 7.14 (t, 1H); MS m/z (relative intensity) 277 (M+, 2), 218 (6), 176 (100).

後処理

  1. filtrationfiltered through a pad of Celite
  2. washrinsed with methanol
  3. additionConcentrated H2SO4 (2.0 mL) was added to the filtrate
  4. temperatureto reflux under nitrogen overnight
  5. customAfter removal of excess methanol
  6. additionthe residue was treated with saturated Na2CO3 (150 mL)
  7. extractionextracted with ethyl acetate (2×200 mL)
  8. extractionThe organic extract
  9. washwas washed with water
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated

出典と根拠

ORDレコード
ord-dae6c3e96cb84550895e2a450a6463c5
出典データセット
uspto-grants-2007_04
特許番号
US07199243B2

反応ノート

読み込み中…