N-[2-(4-benzyloxylphenyl)-2-hydroxyethyl)propionamide → 1-(4-Benzyloxyphenyl)-2-propylaminoethanol

HRID 600228ノート

反応式

HRID 600228 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([OH:22])[CH2:16][NH:17][C:18](=O)[CH2:19][CH3:20])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]([OH:22])[CH2:16][NH:17][CH2:18][CH2:19][CH3:20])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

3

反応物 1

HCID 59645258N-[2-(4-benzyloxylphenyl)-2-hydroxyethyl)propionamide

生成物 1

HCID 574406901-(4-Benzyloxyphenyl)-2-propylaminoethanol収率 99%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To the amide from example 25 (27.5 g, 0.092 mol) in dry THF (100 ml) was added borane-methyl sulphide complex (17.5 ml, 0.18 mol) and the reaction mixture was stirred at reflux for 2 hours. The reaction mixture was cooled then quenched with methanol (30 ml). Water (50 ml) and c.HCl (35 ml) were added and the reaction mixture stirred until all bubbling ceased before concentrating in vacuo. To the residue water (250 ml) was added, before basifying by addition of NH4OH (30 ml). The aqueous layer was extracted with ethyl acetate (3×200 ml) and the combined organic extracts dried over anhydrous magnesium sulphate, filtered and concentrated in vacuo to give the title compound as a white solid (26.1 g 0.09 mol, 99%). 1H NMR (CD3OD, 400 MHz) δ: 0.95 (t, 3H), 1.58 (q, 2H), 2.62 (m, 2H), 2.81 (m, 2H), 4.72 (dd, 1H), 5.05 (s, 2H), 6.95 (d, 2H), 7.24 (m, 3H), 7.35 (t, 2H), 7.41 (d, 2H).

後処理

  1. temperatureat reflux for 2 hours
  2. temperatureThe reaction mixture was cooled
  3. customthen quenched with methanol (30 ml)
  4. additionHCl (35 ml) were added
  5. stirringthe reaction mixture stirred until all bubbling
  6. concentrationbefore concentrating in vacuo
  7. additionTo the residue water (250 ml) was added
  8. additionbefore basifying by addition of NH4OH (30 ml)
  9. extractionThe aqueous layer was extracted with ethyl acetate (3×200 ml)
  10. dry with materialthe combined organic extracts dried over anhydrous magnesium sulphate
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-4733126ec60d4090905648290fc419ca
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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