Sodium borohydride → HCID 69949973, compound

HRID 1397406Notes

Reaction equation

HRID 1397406 reaction equation
[CH3:1][N:2]([CH3:20])[CH2:3][CH2:4][CH:5]([C:8]1[N:9]=[C:10]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[O:11][CH:12]=1)[C:6]#[N:7].[BH4-].[Na+]>CO.[Co](Cl)Cl>[F:19][C:16]1[CH:15]=[CH:14][C:13]([C:10]2[O:11][CH:12]=[C:8]([CH:5]([CH2:6][NH2:7])[CH2:4][CH2:3][N:2]([CH3:20])[CH3:1])[N:9]=2)=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 67323446HCID 67323446, compound

Product 1

HCID 69949973HCID 69949973, compoundYield 44.5%

Reagents, catalysts & solvents 2

HCID 24288Cobalt(II) chlorideCatalystHCID 887MethanolSolvent

Procedure

Cobalt (II) chloride (380 mg, 2.9 mmol) was added to a solution of 4-(dimethylamino)-2-(2-(4-fluorophenyl)oxazol-4-yl)butanenitrile (400 mg, 1.46 mmol) in dry methanol (10 mL) at 0° C., followed by sodium borohydride (550 mg, 14.6 mmol) portionwise. The resulting mixture was stirred at room temperature for 1 h, then quenched carefully with ice water, and filtered through a Celite bed. The filtrate was concentrated under reduced pressure to afford crude 3-(2-(4-fluorophenyl)oxazol-4-yl)-N1,N1-dimethylbutane-1,4-diamine (180 mg, crude), which was carried through without further purification. MS (ESI) m/z: Calculated for C15H20FN3O: 277.16. found: 278.2 (M+H)+.

Workup

  1. customquenched carefully with ice water
  2. filtrationfiltered through a Celite bed
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-41bf5f6382254de2b5e6aff8d22e3d45
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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