Water → HCID 12914029, compound

HRID 867089Notes

Reaction equation

HRID 867089 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:19])([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[CH2:9][C:10]([NH2:12])=O)=[CH:4][CH:3]=1.[BH4-].[Na+].B(F)(F)F.CCOCC.O>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:19])([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[CH2:9][CH2:10][NH2:12])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8000Boron trifluoride etherateHCID 4311764Sodium borohydrideHCID 13020124HCID 13020124, compound

Product 1

HCID 12914029HCID 12914029, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 1.0 g (3.1 mmole) of 3-(4-bromophenyl)-3-hydroxy-3-(3-pyridyl)-propionamide and 0.8 g (0.02 mole) of sodium borohydride in 60 ml of dry tetrahydrofuran at 0° C. and under N2, was added dropwise over 20 minutes 4.6 g (0.03 mole) of boron trifluoride ethyl etherate in 20 ml of dry tetrahydrofuran. The mixture was stirred for 48 hours at room temperature, and then cautiously hydrolyzed with water. Alcalization with 2M NaOH and extraction with ether gave after evaporation a semi-crystalline residue. Recrystallization from ether-petroleum ether gave 0.6 g (63%) of the amine, m.p. 95°-115° C. NMR-spectrum (COCl3): 2H(2.4, 1-CH2)m : 2H(3.0, 2-CH2)m : 3H(3.6, --OH, --NH2)b : 6H(7.1-8.0 ArH)m : 2H(8.6)m ##STR31##

Workup

  1. extractionAlcalization with 2M NaOH and extraction with ether
  2. customgave
  3. customafter evaporation a semi-crystalline residue
  4. customRecrystallization from ether-petroleum ether

Sources & evidence

ORD record
ord-4fc9fe87ec9b4ba5a4500e50f0af0e0e
Source dataset
uspto-grants-1978_07
Patent number
US04102887

Reaction notes

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