Metoprolol → (S)-Metoprolol

HRID 1087281

Reaction equation

HRID 1087281 reaction equation
[CH3:1][CH:2]([NH:4][CH2:5][CH:6]([OH:19])[CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][O:17][CH3:18])=[CH:13][CH:14]=1)[CH3:3].C(O)(=O)/C=C/C=C/C>CC(C)=O>[CH3:3][CH:2]([NH:4][CH2:5][C@H:6]([OH:19])[CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][O:17][CH3:18])=[CH:13][CH:14]=1)[CH3:1]

Participants

4

Reactant 2

HCID 4171MetoprololHCID 643460Sorbic Acid

Product 1

HCID 157716(S)-MetoprololYield 115.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
0 °C

Procedure

To the stirred acetone solution of metoprolol base (19.3 mol), acetone (30 l) and sorbic acid (2.12 kg, 18.9 mol) were added at room temperature. The mixture was heated to reflux and the hot solution was filtered. The filtrate was allowed to cool slowly to 0° C. The crystals were centrifugated off, washed with cold acetone (10 l) and dried for three days in vacuo at room temperature to yield 5.95 kg of crystalline (S)-metoprolol. (81% from (4)).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. filtrationthe hot solution was filtered
  4. washwashed with cold acetone (10 l)
  5. customdried for three days in vacuo at room temperature

Sources & evidence

ORD record
ord-ecc3204946d546b58f26672c8d79018c
Source dataset
uspto-grants-1991_07
Patent number
US05034535

Linked notes

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