Acetic Acid → HCID 18673079, compound

HRID 1058096Notes

Reaction equation

HRID 1058096 reaction equation
C(O)(=O)C.[NH2:5][C:6]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)=[CH:7][C:8]([O:10][CH3:11])=[O:9].[BH4-].[Na+].[ClH:20]>C1COCC1.CO>[ClH:20].[ClH:20].[NH2:5][CH:6]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)[CH2:7][C:8]([O:10][CH3:11])=[O:9]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 69944552Methyl 3-amino-3-(pyridin-3-YL)prop-2-enoate

Product 1

HCID 18673079HCID 18673079, compoundYield 89.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-2.5 °C

Procedure

Glacial acetic acid (526.9 g, 8.78 mol) was added dropwise at <−5° C. to a suspension of methyl 3-amino-3-(3-pyridyl)-2-propenoate (0.45 mol) and sodium borohydride (44.3 g, 1.17 mol) in THF (500 g) and the resulting reaction mixture was stirred at −5-0° C. After 5 h, methanol (600 g) was added dropwise to the solution at −5-0° C. After 0.5 hours, HCl (163 g, 4.47 mol) was bubbled through the solution and stirred at 0° C. After 8 h, the white precipitate was filtered off and dried at 40° C. to yield 101.6 g (89%) of methyl 3-Amino-3-(3-pyridyl)propanoate dihydrochloride.

Workup

  1. customthe resulting reaction mixture
  2. waitAfter 0.5 hours
  3. stirringstirred at 0° C
  4. waitAfter 8 h
  5. filtrationthe white precipitate was filtered off
  6. customdried at 40° C.

Sources & evidence

ORD record
ord-d42a7e7618dc4ebda6c1abbb4aa23d84
Source dataset
uspto-grants-2003_02
Patent number
US06515130B1

Reaction notes

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