Sodium borohydride → HCID 21357383, compound

HRID 1275196Notes

Reaction equation

HRID 1275196 reaction equation
[Br-].[OH:2][CH2:3][CH2:4][CH2:5][N+:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:8][CH:7]=1.[BH4-].[Na+]>CCO>[N:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:9]1[CH2:10][CH2:11][N:6]([CH2:5][CH2:4][CH2:3][OH:2])[CH2:7][CH:8]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22993556HCID 22993556, compound

Product 1

HCID 21357383HCID 21357383, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-(3-hydroxypropyl)-4-[pyrid-2-yl]pyridinium bromide (8 g) in 100 mL EtOH was added NaBH4 (1.41 g, 37.2 mmol) in small portions. The reaction mixture was stirred at room temperature for 12 h and then quenched with drops of water. The solvent was removed in vacuo and the residue was purified by column chromatography over silica gel with 1:4 MeOH/EtOAc followed by 1:4 (2M NH3 in MeOH)/EtOAc as the eluting system (Rf =0.6, (2M NH3 in MeOH)/EtOAc=1:4) to obtain 3-(3',6'-dihydro-2'-H-(2,4']bipyridinyl-1'-yl)-propanol as an oil (1.58 g, 39% over two steps).

Workup

  1. customquenched with drops of water
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by column chromatography over silica gel with 1:4 MeOH/EtOAc

Sources & evidence

ORD record
ord-4e34cd573df04cbcace335aebbf7055a
Source dataset
uspto-grants-2000_12
Patent number
US06159990

Reaction notes

Loading…