Water → HCID 59438495, compound

HRID 2177493Notes

Reaction equation

HRID 2177493 reaction equation
[CH3:1][N:2]1[C:7](=S)[CH2:6][CH2:5][C:4]([N+:15]([O-:17])=[O:16])([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[CH2:3]1.[BH4-].[Na+].O>CO>[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][C:4]([N+:15]([O-:17])=[O:16])([C:9]2[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=2)[CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 59438526HCID 59438526, compound

Product 1

HCID 59438495HCID 59438495, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 105 mg (0.418 mmol) rac-1-Methyl-3-nitro-2,3,4,5-tetrahydro-1H-[3,4′]bipyridinyl-6-thione in 2.1 ml methanol was added 144 mg (3.8 mmol) NaBH4. The mixture was stirred at room temperature for 20 minutes. Water (1.0 ml) was added. The mixture was stirred for 1 hour. The methanol was removed in vacuo. The residue was diluted with water and extracted 3 times with dichloromethane. The combined extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The crude oil was purified on silica gel (Eluent: Heptane/ethyl acetate 0 to 100%) to provide 53 mg (57%) of the title compound as a yellow oil. MS (m/e): 222.3 (M+H).

Workup

  1. stirringThe mixture was stirred for 1 hour
  2. customThe methanol was removed in vacuo
  3. additionThe residue was diluted with water
  4. extractionextracted 3 times with dichloromethane
  5. dry with materialThe combined extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude oil was purified on silica gel (Eluent: Heptane/ethyl acetate 0 to 100%)

Sources & evidence

ORD record
ord-f76da9001cdd40d8a21cfc064f22ea69
Source dataset
uspto-grants-2015_06
Patent number
US09067911B2

Reaction notes

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