Borane → 3-Benzyl-6-nitro-3-azabicyclo[3.1.0]hexane

HRID 712481Notes

Reaction equation

HRID 712481 reaction equation
[CH2:1]([N:8]1[C:13](=O)[CH:12]2[CH:10]([CH:11]2[N+:15]([O-:17])=[O:16])[C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B>C1COCC1>[CH2:1]([N:8]1[CH2:9][CH:10]2[CH:12]([CH:11]2[N+:15]([O-:17])=[O:16])[CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6331BoraneHCID 226283243-Benzyl-6-nitro-3-azabicyclo[3.1.0]hexane-2,4-dione

Product 1

HCID 215851823-Benzyl-6-nitro-3-azabicyclo[3.1.0]hexaneYield 80.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-benzyl-6-nitro-3-azabicyclo[3.1.0]hexane-2,4-dione (6.00 g) in THF was added a solution of borane in THF (1 M, 100 mL) dropwise. The reaction mixture was refluxed for 1 h, then cooled to rt and quenched with MeOH. The mixture was concentrated in vacuo and the residue was chromatographed by a silica gel column (eluting agent: 2:1 (v/v) PE/EA) to afford the title compound as pale yellow oil (4.30 g, 80.00%), HPLC: 94.00%. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 219.2 (M+1); 1H NMR (400 MHz, CDCl3) δ: 2.51 (m, 2H), 3.14 (d, J=1.8 Hz, 2H), 3.60 (s, 2H), 4.63 (s, 1H), 7.3 (m, 5H) ppm.

Workup

  1. temperatureThe reaction mixture was refluxed for 1 h
  2. customquenched with MeOH
  3. concentrationThe mixture was concentrated in vacuo
  4. customthe residue was chromatographed by a silica gel column (eluting agent: 2:1 (v/v) PE/EA)

Sources & evidence

ORD record
ord-03bf39ee12134cdabb84f1bda71f76b2
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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