Isopropylamine → Levopropranolol

HRID 981363

반응식

HRID 981363 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 91536Levopropranolol수율 92.6%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-09f86e121b944fc3b6e0dad1e3b70f51
출처 데이터셋
uspto-grants-1991_02
특허 번호
US04990668

연결된 노트

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