Isopropylamine → Levopropranolol

HRID 981363Notes

Reaction equation

HRID 981363 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

HCID 91536LevopropranololYield 92.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-09f86e121b944fc3b6e0dad1e3b70f51
Source dataset
uspto-grants-1991_02
Patent number
US04990668

Reaction notes

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