Reaction #710544

Reaction equation

sodium triacetoxyborohydride

4-fluoroaniline

isobutyraldehyde

→

(4-fluoro-phenyl)-isobutyl-amine

Yield 54.3%

Solvents

DCM

Conditions

Workup

1. 1
   ConcentrationThe reaction was concentrated
2. 2
   workup.DISSOLUTIONdissolved in DCM
3. 3
   DryingMeOH, dry loaded onto silica
4. 4
   Otherthen purified by silica gel column chromatography (0-25% DCM in cyclohexane)

Procedure

To a solution of 4-fluoroaniline (1 g, 9 mmol) in DCM (20 mL) at room temperature was added isobutyraldehyde (985 μL, 10.8 mmol) followed by portionwise sodium triacetoxyborohydride (2.86 g, 13.5 mmol) and the reaction was stirred at room temperature for 64 hours. The reaction was concentrated and then dissolved in DCM and MeOH, dry loaded onto silica then purified by silica gel column chromatography (0-25% DCM in cyclohexane) to give (4-fluoro-phenyl)-isobutyl-amine (817 mg, 54%). LCMS (m/z, Method A) ES+ 168 [M+1]+.

Source