Reaction #1990

Reaction equation

compound

(1-benzyl-pyrroldin-3-yl)-cyclopropyl-methanone

ammonium acetate

NaBH3CN

→

title compound

1-(1-benzyl-pyrroldin-3-yl)-1-cyclopropyl-methylamine

Solvents

methanol

Conditions

Workup

1. 1
   workup.ADDITION1.2 g of 4 Å molecular sieves were added
2. 2
   FiltrationThe mixture was filtered
3. 3
   Washthe sieves washed with methanol
4. 4
   Washthe wash
5. 5
   Concentrationconcentrated
6. 6
   workup.DISSOLUTIONThe residue was dissolved in 100 mL of methylene chloride
7. 7
   workup.ADDITION30 mL of 15% NaOH was added
8. 8
   WashThe organic phase and a second wash of the aqueous phase
9. 9
   Washwashed with water and brine
10. 10
    Dryingdried over MgSO4
11. 11
    OtherThe solvent was removed
12. 12
    Otherthe residue was chromatographed on silica gel

Procedure

A 1 g sample of the compound from step 470b, 3.37 g of ammonium acetate and 274 mg of NaBH3CN were dissolved in 15 mL of methanol, 1.2 g of 4 Å molecular sieves were added, and the mixture was stirred at room temperature under N2 for 16 hours. The mixture was filtered, the sieves washed with methanol, the wash and filtrate combined, and concentrated. The residue was dissolved in 100 mL of methylene chloride, and 30 mL of 15% NaOH was added. The organic phase and a second wash of the aqueous phase were combined and washed with water and brine, then dried over MgSO4. The solvent was removed, and the residue was chromatographed on silica gel to give 460 mg of the title compound.

Source