Methanol → HCID 57419225, compound

HRID 1863447Notes

Reaction equation

HRID 1863447 reaction equation
[CH2:1]1[CH2:3][CH:2]1[NH:4][CH2:5][C:6]([C:8]1[N:9]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])[CH:10]=[CH:11][CH:12]=1)=[O:7].[BH4-].[Na+].CO.O>C(O)(C)C>[CH:2]1([NH:4][CH2:5][CH:6]([C:8]2[N:9]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])[CH:10]=[CH:11][CH:12]=2)[OH:7])[CH2:3][CH2:1]1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 203915152-(2-Cyclopropylamino)acetyl-1-(o-fluorobenzyl)pyrrole

Product 1

HCID 57419225HCID 57419225, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
85 °C

Procedure

A solution of 8.0 g of 2-(2-cyclopropylamino)-acetyl-1-(o-fluorobenzyl)pyrrole, free base of a, in 100 ml of isopropyl alcohol is added to a suspension of 2.2 g sodium borohydride in 100 ml of isopropranol. The reaction mixture is refluxed at 85° C. for 4 hours, allowed to cool to ambient temperature and 50 ml of methanol introduced. The solvent is removed leaving a yellow semi-solid which is treated with water and then extracted into ether. The ether extract is washed with water, dried and filtered and the solvent removed leaving a pure yellow oil of 2-(cyclopropylamino)-1-[1-(o-fluorobenzyl)-2-pyrryl]ethanol. Infrared and nuclear magnetic resonance spectra confirm this structure.

Workup

  1. temperatureto cool to ambient temperature
  2. customThe solvent is removed
  3. customleaving a yellow semi-solid which
  4. extractionextracted into ether
  5. extractionThe ether extract
  6. washis washed with water
  7. customdried
  8. filtrationfiltered
  9. customthe solvent removed

Sources & evidence

ORD record
ord-14558edaa95c41018d1083b1cf68c6c9
Source dataset
uspto-grants-1979_09
Patent number
US04169095

Reaction notes

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