Methanol → 2-(2-Bromoisonicotinoylamino)-3-(3,4-dimethoxyphenyl)-1-propanol

HRID 1739435Notes

Reaction equation

HRID 1739435 reaction equation
C([O:3][C:4](=O)[C@H:5]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=1)[NH:6][C:7](=[O:15])[C:8]1[CH:13]=[CH:12][N:11]=[C:10]([Br:14])[CH:9]=1)C.[BH4-].[Na+].CO.O>O1CCCC1>[Br:14][C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][N:11]=1)[C:7]([NH:6][CH:5]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=1)[CH2:4][OH:3])=[O:15]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 53678990N-(2-bromoisonicotinoyl)-3-(3,4-dimethoxyphenyl)alanine ethyl ester

Product 1

HCID 218408112-(2-Bromoisonicotinoylamino)-3-(3,4-dimethoxyphenyl)-1-propanolYield 88.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(2-bromoisonicotinoyl)-3-(3,4-dimethoxyphenyl)alanine ethyl ester (12.8 g) in tetrahydrofuran (100 ml) is added sodium borohydride (3.3 g), and thereto is added dropwise methanol (15 ml) with heating under reflux over a period of three hours. The reaction mixture is cooled with ice, and thereto is added water. The mixture is extracted with chloroform, and the extract is washed, dried, and concentrated to give 2-(2-bromoisonicotinoylamino)-3-(3,4-dimethoxyphenyl)-1-propanol (10.2 g).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux over a period of three hours
  3. temperatureThe reaction mixture is cooled with ice
  4. extractionThe mixture is extracted with chloroform
  5. washthe extract is washed
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ac3eca234ea841d6b08ddd88dba774de
Source dataset
uspto-grants-1999_10
Patent number
US05965730

Reaction notes

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