Water → HCID 12914029, compound

HRID 2052678Notes

Reaction equation

HRID 2052678 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. Alkalization with 2 M 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 ##STR30##

Workup

  1. extractionAlkalization with 2 M 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-5f9a94eb73dc42709822a445c55b449a
Source dataset
uspto-grants-1980_01
Patent number
US04186202

Reaction notes

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