Potassium Carbonate → 3-Benzyl-6-nitro-3-azabicyclo[3.1.0]hexane-2,4-dione

HRID 712480

Reaction equation

HRID 712480 reaction equation
[CH2:1]([N:8]1[C:12](=[O:13])[CH:11]=[CH:10][C:9]1=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:22][N+:23]([O-:25])=[O:24]>CC#N>[CH2:1]([N:8]1[C:12](=[O:13])[CH:11]2[CH:10]([CH:22]2[N+:23]([O-:25])=[O:24])[C:9]1=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 68423BromonitromethaneHCID 74204Benzylmaleimide

Product 1

HCID 226283243-Benzyl-6-nitro-3-azabicyclo[3.1.0]hexane-2,4-dioneYield 40.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of N-benzylmaleimide (7.40 g) and K2CO3 (5.50 g) in 500 mL of CH3CN was added bromonitromethane (5.60 g) dropwise. The reaction mixture was stirred for 24 h at room temperature and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 4:1 (v/v) PE/EA) to give the title compound as a pale yellow solid (3.90 g, 40.00%), HPLC: 93.00%. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 247.1 (M+1); 1H NMR (400 MHz, CDCl3) δ: 3.34 (d, J=1.8 Hz, 2H), 4.51 (t, J=1.6 Hz, 1H), 4.53 (s, 2H), 7.22-7.42 (m, 5H) ppm.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue was chromatographed with a silica gel column (eluting agent: 4:1 (v/v) PE/EA)

Sources & evidence

ORD record
ord-7dcd014e23f94b93bb4a185fc6a29b56
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Linked notes

Loading…