Hydrochloric Acid → Hydroxyterfenadine

HRID 1266625ノート

反応式

HRID 1266625 の反応式
[O:1]=[C:2]([C:26]1[CH:31]=[CH:30][C:29]([C:32]([CH3:36])([CH3:35])[CH2:33][OH:34])=[CH:28][CH:27]=1)[CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([C:12]([OH:25])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][CH2:7]1.[BH4-].[Na+].Cl>CO.O>[OH:1][CH:2]([C:26]1[CH:27]=[CH:28][C:29]([C:32]([CH3:36])([CH3:35])[CH2:33][OH:34])=[CH:30][CH:31]=1)[CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([C:12]([OH:25])([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:8][CH2:7]1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 118129062-(4-(1-Oxo-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)-butyl)-phenyl)-2-methylpropanol

生成物 1

HCID 9805485Hydroxyterfenadine収率 79%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒2 回

実験手順

Dissolve 2-(4-(1-oxo-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)-butyl)-phenyl)-2-methylpropanol in methanol (450 mL) and stir for 15 minutes at room temperature. Add, -by dropwise addition, a solution of sodium borohydride (2.25 g, 0.06 mol) in water (10 mL) over 15 minutes. Stir for another 30 minutes and cool in an ice-bath. Slowly add concentrated hydrochloric acid (4 mL) and water (8 mL) and stir for an additional 20 minutes. Evaporate the solvent in vacuo and partition the residue between methylene chloride (150 mL) and water (70 mL). Separate the organic phase and extract the aqueous phase with methylene chloride (25 mL). Wash the combined organic layers with water (2×50 mL), evaporate the solvent in vacuo and recrystallize (acetone) to give the title compound as white needles (9.53 g, 79%).

後処理

  1. additionAdd, -by dropwise addition
  2. stirringStir for another 30 minutes
  3. temperaturecool in an ice-bath
  4. stirringstir for an additional 20 minutes
  5. customEvaporate the solvent in vacuo
  6. custompartition the residue between methylene chloride (150 mL) and water (70 mL)
  7. customSeparate the organic phase
  8. extractionextract the aqueous phase with methylene chloride (25 mL)
  9. washWash the combined organic layers with water (2×50 mL)
  10. customevaporate the solvent in vacuo
  11. customrecrystallize (acetone)

出典と根拠

ORDレコード
ord-fe1b072cee3d4c89b223aa959d60c605
出典データセット
uspto-grants-2003_04
特許番号
US06548675B2

反応ノート

読み込み中…