Sodium borohydride → HCID 59487296, compound

HRID 1925552Notes

Reaction equation

HRID 1925552 reaction equation
[BH4-].[Na+].[CH3:3][C:4]([CH3:29])([CH3:28])[C:5](=[O:27])[CH2:6][NH:7][C:8]([C:10]1[C:11]([S:16][CH2:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[N:12][CH:13]=[CH:14][CH:15]=1)=[O:9].CCCCCC.CC(=O)OCC>CCO>[F:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][CH2:18][CH2:17][S:16][C:11]2[C:10]([C:8]([NH:7][CH2:6][CH:5]([OH:27])[C:4]([CH3:28])([CH3:3])[CH3:29])=[O:9])=[CH:15][CH:14]=[CH:13][N:12]=2)=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 21226206Ethyl acetate hexaneHCID 67521469HCID 67521469, compound2×

Product 1

HCID 59487296HCID 59487296, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

70 mg (1.8 mmol) of NaBH4 were added in portions at 0° C. to a solution of 350 mg (0.9 mmol) of N-(3,3-dimethyl-2-oxo-butyl)-2-[3-(4-fluoro-phenyl)-propylsulfanyl]-pyridine-3-carboxylic acid amide (exemplary compound 125) in EtOH (7 ml). Stirring was then carried out for 2 h at RT. The mixture was then cooled to 0° C., quenched with a sat. aq. NH4Cl sol. (20 ml) and concentrated in vacuo. The residue was taken up in EA and the solution was washed with a 1M aq. NaHCO3 sol., water and brine, dried over Na2SO4, filtered and concentrated in vacuo. CC (hexane/EA 3:2) of the residue yielded 320 mg (0.82 mmol, 91%) of 2-[3-(4-fluorophenyl)-propylsulfanyl]-N-(2-hydroxy-3,3-dimethyl-butyl)-pyridine-3-carboxylic acid amide. MS: m/z 391.2 [M+H]+.

Workup

  1. customquenched with a sat. aq. NH4Cl sol. (20 ml)
  2. concentrationconcentrated in vacuo
  3. washthe solution was washed with a 1M aq. NaHCO3 sol., water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e26675737c4d49f6a7952eecab47658d
Source dataset
uspto-grants-2012_05
Patent number
US08178684B2

Reaction notes

Loading…