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

HRID 2079774Notes

Reaction equation

HRID 2079774 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.Br[CH2:16][N+:17]([O-:19])=[O:18].C([O-])([O-])=O.[K+].[K+].C(Cl)Cl.CCCCCCC>CC#N>[CH2:1]([N:8]1[C:12](=[O:13])[CH:11]2[CH:10]([CH:16]2[N+:17]([O-:19])=[O:18])[C:9]1=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 68423Bromonitromethane3×HCID 74204BenzylmaleimideHCID 21907733Dichloromethane heptane

Product 1

HCID 226283243-Benzyl-6-nitro-3-azabicyclo[3.1.0]hexane-2,4-dioneYield 45.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of N-benzylmaleimide (5.0 g, 26.7 mmol) in MeCN (334 ml) was added bromonitromethane (1.87 ml, 26.7 mmol). K2CO3 (3.69 g, 26.7 mmol) was added and the reaction mixture vigorously stirred at r.t. After 4 h an additional portion of bromonitromethane (0.2 ml) was added. Further addition of bromonitromethane (0.2 ml) was added at further 4 h intervals (×4). After 48 h, TLC (50% DCM/heptane) indicated reaction completion. The reaction mixture was evaporated to dryness. The brown residue was purified by column chromatography (100% DCM), giving the title compound as a white solid (3.0 g, 42%). 1H NMR (300 MHz, CDCl3) δ: 3.35 (2H, s), 4.50 (1H, s), 4.55 (2H, s), 7.2-7.4 (5H, m).

Workup

  1. additionwas added at further 4 h intervals (×4)
  2. customreaction completion
  3. customThe reaction mixture was evaporated to dryness
  4. customThe brown residue was purified by column chromatography (100% DCM)

Sources & evidence

ORD record
ord-fd0df75ef7764f64821125db7f8f2654
Source dataset
uspto-grants-2011_04
Patent number
US07932246B2

Reaction notes

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