Isopropylamine → (S)-Metoprolol

HRID 1031846Notes

Reaction equation

HRID 1031846 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][O:14][CH3:15])=[CH:8][CH:7]=1)[CH:2]1[O:4][CH2:3]1.[CH:16]([NH2:19])([CH3:18])[CH3:17]>C(O)C>[CH3:17][CH:16]([NH:19][CH2:3][C@H:2]([OH:4])[CH2:1][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][O:14][CH3:15])=[CH:8][CH:7]=1)[CH3:18]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 92515((p-(2-Methoxyethyl)phenoxy)methyl)oxirane

Product 1

HCID 157716(S)-Metoprolol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

171 mg of (+)-4-(2-methoxyethyl)-phenyl glycidyl ether were reacted with isopropylamine (method as in Example 2) to obtain 154 mg of (-)-metoprolol melting at 44-45° C. with [α]D25= - 5.27° (c =0.967 in ethanol). Optical purity was determined to be 98.4% based on HPLC of the S-leucyl diastereomeric derivatives as in Example 2. Evaporation of the mother liquor gave 6 mg of (-)-metoprolol of 92.2% optical purity.

Sources & evidence

ORD record
ord-b91eeeb0e6b841c1b3b5e04f5224906b
Source dataset
uspto-grants-1990_09
Patent number
US04956284

Reaction notes

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