Sodium borohydride → (S)-6-(2-methylpyrrolidin-1-yl)-2-(trifluoromethyl)pyridin-3-amine

HRID 2404902Notes

Reaction equation

HRID 2404902 reaction equation
[CH3:1][C@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[N:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[C:10]([N+:17]([O-])=O)=[CH:9][CH:8]=1.[BH4-].[Na+]>CO>[CH3:1][C@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[N:12]=[C:11]([C:13]([F:16])([F:14])[F:15])[C:10]([NH2:17])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59410063(S)-6-(2-methylpyrrolidin-1-yl)-3-nitro-2-(trifluoromethyl)pyridine

Product 1

HCID 59410113(S)-6-(2-methylpyrrolidin-1-yl)-2-(trifluoromethyl)pyridin-3-amineYield 97.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-6-(2-methylpyrrolidin-1-yl)-3-nitro-2-(trifluoromethyl)pyridine (300 mg, 1.1 mmoL) in 5 mL methanol was added NiCl2.6H2O (772 mg, 3.3 mmoL). After stirring for 5 min, NaBH4 (84 mg, 2.2 mmoL) was added in three portions at 0° C. The reaction mixture was stirred for 5 min and quenched with water (10 mL) and was extracted with EtOAc (15 mL×3). The combined organic layer was washed with brine, dried over anhydrous Na2SO4, concentrated and purified by silica gel chromatography on silica gel to afford (S)-6-(2-methylpyrrolidin-1-yl)-2-(trifluoromethyl)pyridin-3-amine (260 mg, 92.6% yield).

Workup

  1. stirringThe reaction mixture was stirred for 5 min
  2. customquenched with water (10 mL)
  3. extractionwas extracted with EtOAc (15 mL×3)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. custompurified by silica gel chromatography on silica gel

Sources & evidence

ORD record
ord-abd308e942a54993b4ea6c04397f41f2
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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