Reaction #487585

Reaction equation

Pyrrolidine

2-nitro-5,6,8,9-tetrahydro-benzocyclohepten-7-one

NaBH(OAc)3

AcOH

→

1-(2-nitro-6,7,8,9-tetrahydro-5H-benzo[7]annulen-7-yl)pyrrolidine

Solvents

1,2-dichloroethane

Conditions

Workup

1. 1
   OtherThe reaction mixture was quenched with saturated NaHCO3
2. 2
   Extractionthe product was extracted with EtOAc (3×30 mL)
3. 3
   Dryingdried over NaSO4
4. 4
   OtherThe solvent was evaporated
5. 5
   Otherthe residue was purified by flash column chromatography
6. 6
   Washeluting with CH2Cl2/DMA=1/1 (DMA=CH2Cl2/MeOH/30% NH3=80/19/1)

Procedure

Pyrrolidine (0.85 g, 12 mmol) and 2-nitro-5,6,8,9-tetrahydro-benzocyclohepten-7-one (2.05 g, 10 mmol) were mixed in 1,2-dichloroethane (35 mL) and then treated with NaBH(OAc)3 (3.18 g, 15 mmol) and AcOH (0.60 g, 10 mmol). The mixture was stirred at ambient temperature under a N2 atmosphere overnight. The reaction mixture was quenched with saturated NaHCO3, and the product was extracted with EtOAc (3×30 mL). The organic layers were combined and dried over NaSO4. The solvent was evaporated and the residue was purified by flash column chromatography eluting with CH2Cl2/DMA=1/1 (DMA=CH2Cl2/MeOH/30% NH3=80/19/1) to afford 1-(2-nitro-6,7,8,9-tetrahydro-5H-benzo[7]annulen-7-yl)pyrrolidine, a yellow oil (2.2 g, 85%); MS (m/e): 261 (M+H+).

Source