Reaction #1833267

Reaction equation

1-(benzyloxy)-4-[(trans)-2-nitrocyclopropyl]benzene

Intermediate C

1-(benzyloxy)-4-[(trans)-2-nitrocyclopropyl]benzene

HCl

→

(trans)-2-[4-(benzyloxy)phenyl]cyclopropanamine

Yield 70.0%

Solvents

i-PrOH

Conditions

Workup

1. 1
   FiltrationAfter 17 h the mixture was filtered through a pad of celite that
2. 2
   Washwas washed with 10 mL of methanol
3. 3
   ConcentrationThe filtrate was concentrated
4. 4
   workup.ADDITION10 mL of water were added
5. 5
   Washwashing with CH2Cl2 (3×15 mL)
6. 6
   DryingThe organic layers were dried over anhydrous Na2SO4
7. 7
   Filtrationfiltered
8. 8
   OtherAfter removal of the solvent
9. 9
   Otherthe crude product was purified by column chromatography on silica gel (10% MeOH/CH2Cl2)

Procedure

Zn dust (1.97 g, 30 mol) was added in small portions, over a period of 30 min, to a vigorously stirred solution of 1-(benzyloxy)-4-[(trans)-2-nitrocyclopropyl]benzene (Intermediate C, 0.81 g, 3.0 mmol) in i-PrOH (25 mL) and HCl (11 mL of aqueous solution 2.7 N, 30 mmol). After 17 h the mixture was filtered through a pad of celite that was washed with 10 mL of methanol. The filtrate was concentrated and 10 mL of water were added, washing with CH2Cl2 (3×15 mL). The organic layers were dried over anhydrous Na2SO4 and filtered. After removal of the solvent, the crude product was purified by column chromatography on silica gel (10% MeOH/CH2Cl2) affording 0.50 g of (trans)-2-[4-(benzyloxy)phenyl]cyclopropanamine [Rf=0.2 (10% MeOH/CH2Cl2), white solid, 70% yield]. 1H NMR δ (ppm): MeOH 400 MHz: 7.45-7.27 (m, 5H, ArH); 6.96 (d, J=8.5 Hz, 2H, ArH); 6.86 (d, 8.5 Hz, 2H, ArH); 5.03 (s, 2H, CH2); 2.41-2.34 (m, 1H, CH); 1.86-1.76 (m, 1H, CH); 0.98-0.85 (m, 2H, CH2).

Source