Methanol → HCID 90281909, compound

HRID 1497520Notes

Reaction equation

HRID 1497520 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:13]=[C:14]([F:16])[CH:15]=1)[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])#[N:2].CO.O.[BH4-].[Na+]>O1CCCC1.[Co](Cl)Cl>[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]([CH:13]=[C:14]([F:16])[CH:15]=1)[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 90281957HCID 90281957, compound

Product 1

HCID 90281909HCID 90281909, compoundYield 47.8%

Reagents, catalysts & solvents 2

HCID 24288Cobalt(II) chlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a mixed solution of tert-butyl 3-cyano-5-fluorobenzoate (3.00 g) in tetrahydrofuran (60.0 mL)-methanol (30.0 mL) was added a mixture of cobalt (II) chloride (4.40 g) and water (60.0 mL) under ice-cooling, and then sodium borohydride (1.54 g) was added under an argon flow, followed by stirring at room temperature for 30 minutes. The insoluble material was filtered through Celite and then washed with a mixed solvent of tetrahydrofuran-methanol-water (2:1:2, and then the filtrate was concentrated under reduced pressure. To the residue was added a saturated aqueous sodium chloride solution, followed by extraction with chloroform. The organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (chloroform-methanol) to obtain tert-butyl 3-(aminomethyl)-5-fluorobenzoate (1.46 g).

Workup

  1. temperaturecooling
  2. filtrationThe insoluble material was filtered through Celite
  3. washwashed with a mixed solvent of tetrahydrofuran-methanol-water (2:1:2
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionTo the residue was added a saturated aqueous sodium chloride solution
  6. extractionfollowed by extraction with chloroform
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by basic silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-803e3454c74c4a19b019e1b7626324b6
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

Loading…