Sodium borohydride → 2-{4-[4-nitro-3-(propan-2-yloxy)phenyl]-3,6-dihydropyridin-1(2H)-yl}ethanol

HRID 518867Notes

Reaction equation

HRID 518867 reaction equation
[BH4-].[Na+].[I-].[OH:4][CH2:5][CH2:6][N+:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[C:15]([O:22][CH:23]([CH3:25])[CH3:24])[CH:14]=2)=[CH:9][CH:8]=1>CO.O>[N+:19]([C:16]1[CH:17]=[CH:18][C:13]([C:10]2[CH2:11][CH2:12][N:7]([CH2:6][CH2:5][OH:4])[CH2:8][CH:9]=2)=[CH:14][C:15]=1[O:22][CH:23]([CH3:25])[CH3:24])([O-:21])=[O:20]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 866980191-(2-Hydroxyethyl)-4-[4-nitro-3-(propan-2-yloxy)phenyl]pyridinium iodide

Product 1

HCID 866980212-{4-[4-nitro-3-(propan-2-yloxy)phenyl]-3,6-dihydropyridin-1(2H)-yl}ethanolYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 887MethanolSolvent

Procedure

A mixture of 100 mg of 4-[4-nitro-3-(propan-2-yloxy)phenyl]pyridine (see method 1) and 0.075 ml of 2-iodoethanol in 1.7 ml of acetonitrile is heated at 85° C. (bath) for 1 h. 75 μl of 2-iodoethanol are then added and the heating is continued for 15 h at 91° C. The mixture is then concentrated under vacuum, so as to obtain a solid which is taken up with 10 ml of ethyl ether. The resulting heterogeneous mixture is filtered and the solid is rinsed with ethyl ether and dried under reduced pressure, so as to obtain 147 mg of 1-(2-hydroxyethyl)-4-[4-nitro-3-(propan-2-yloxy)phenyl]pyridinium iodide in the form of a solid. 44 g of sodium borohydride are added, at a temperature of about 0° C. (ice/water bath) to a solution of 0.142 g of 1-(2-hydroxyethyl)-4-[4-nitro-3-(propan-2-yloxy)phenyl]pyridinium iodide in 2.6 ml of methanol. After 30 minutes, a few drops of water are added and the mixture is left to return to ambient temperature. The mixture is concentrated to dryness under reduced pressure and then diluted with 150 ml of ethyl acetate. The organic phase is washed successively with 120 ml of a saturated sodium hydrogen carbonate solution and then 70 ml of a saturated sodium chloride solution. The organic phase is dried over anhydrous magnesium sulfate, filtered and then concentrated to dryness under reduced pressure, so as to obtain 90 mg of 2-{4-[4-nitro-3-(propan-2-yloxy)phenyl]-3,6-dihydropyridin-1(2H)-yl}ethanol.

Workup

  1. waitthe mixture is left
  2. customto return to ambient temperature
  3. concentrationThe mixture is concentrated to dryness under reduced pressure
  4. additiondiluted with 150 ml of ethyl acetate
  5. washThe organic phase is washed successively with 120 ml of a saturated sodium hydrogen carbonate solution
  6. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-80dd0ddea4184b2aac94a6d7bf3b144b
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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