Isopropylamine → Levopropranolol

HRID 981363

反応式

HRID 981363 の反応式
[C:1]1([O:11][CH2:12][C@H:13]2[O:15][CH2:14]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH:16]([NH2:19])([CH3:18])[CH3:17]>CO>[CH3:17][CH:16]([NH:19][CH2:14][C@H:13]([OH:15])[CH2:12][O:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)[CH3:18]

参加物

4

反応物 2

HCID 6363IsopropylamineHCID 148933(2S)-2-((1-Naphthalenyloxy)methyl)oxirane

生成物 1

HCID 91536Levopropranolol収率 92.6%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of (S)-(+)-glycidyl naphthyl ether (20 g, 0.1 m) and isopropylamine (10 g, 0.17 m) in methanol (100 mL) was refluxed for 1 hour and evaporated to dryness. The residue was taken up with ether (200 mL), washed with water and dried over MgSO4. After filtering, the filtrate was acidified with gaseous HCl. The crude solid was recrystallized from ethanol to afford 24 g (81%) of pure 1-propranolol, mp 198°-200° C., [α]D25 -26.8 (c 1, EtOH). NMR and IR were consistent with the assigned structure.

後処理

  1. customevaporated to dryness
  2. washwashed with water
  3. dry with materialdried over MgSO4
  4. filtrationAfter filtering
  5. customThe crude solid was recrystallized from ethanol

出典と根拠

ORDレコード
ord-09f86e121b944fc3b6e0dad1e3b70f51
出典データセット
uspto-grants-1991_02
特許番号
US04990668

関連ノート

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