Hydrogen Bromide → Terbutaline

HRID 1578632Notes

Reaction equation

HRID 1578632 reaction equation
Br.C([O:5][C:6]1[CH:7]=[C:8]([CH:16]([OH:23])[CH2:17][NH:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:9]=[C:10]([O:12]C(=O)C)[CH:11]=1)(=O)C.O.CCOCC>C(O)C.[Pd]>[OH:5][C:6]1[CH:7]=[C:8]([CH:16]([OH:23])[CH2:17][NH:18][C:19]([CH3:21])([CH3:20])[CH3:22])[CH:9]=[C:10]([OH:12])[CH:11]=1

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 962WaterHCID 3283Diethyl EtherHCID 21450028HCID 21450028, compound

Product 1

HCID 5403Terbutaline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1.1 g of this salt were dissolved in warm absolute ethanol and 0.1 g 10% palladium charcoal were added. The solution was then hydrogenated at 50°C. and 5 atmospheres pressure overnight. The catalyst was filtered off and the volume of the solution reduced by evaporation. The hydrobromide of 1-(3',5'-diacetoxyphenyl)-2-(t-butylamino)-ethanol with 1 mole of water was precipitated by the addition of ether. M.p. 108°-111°C. The protective acetyl groups may be removed by boiling the 1-(3',5'-diacetoxyphenyl)-2-(t-butylamino)-ethanol hydrobromide with 1% hydrobromic acid for three hours. After evaporation and drying the product was recrystallized as described in Example 2c.

Workup

  1. customwas then hydrogenated at 50°C.
  2. custom5 atmospheres pressure overnight
  3. filtrationThe catalyst was filtered off
  4. customthe volume of the solution reduced by evaporation
  5. customThe protective acetyl groups may be removed
  6. customfor three hours
  7. customAfter evaporation
  8. customdrying the product
  9. customwas recrystallized

Sources & evidence

ORD record
ord-4bf788f4a52546c5a3c6af9d21f00452
Source dataset
uspto-grants-1976_02
Patent number
US03937838

Reaction notes

Loading…