Borane;tetrahydrofuran → HCID 22141201, compound

HRID 428970Notes

Reaction equation

HRID 428970 reaction equation
[CH2:1]([N:7]1[C:12](=O)[CH:11]2[CH:9]([C:10]2([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=2)[C:14]#[N:15])[C:8]1=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].B.O1CCCC1>O1CCCC1>[CH2:1]([N:7]1[CH2:8][CH:9]2[CH:11]([C:10]2([CH2:14][NH2:15])[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=2)[CH2:12]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 221412573-Hexyl-6-(3-nitrophenyl)-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carbonitrile

Product 1

HCID 22141201HCID 22141201, compoundYield 116.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-hexyl-6-(3-nitrophenyl)-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carbonitrile (Preparation 111, 250 mg, 0.732mmol) in anhydrous tetrahydrofuran (3 ml) stirred under nitrogen was added dropwise borane-tetrahydrofuran complex (1.0 M in tetrahydrofuran, 2.9 ml, 2.9 mmol). The reaction mixture was heated at reflux for 2 h, before cooling and quenching with dry methanol (2 ml). The solution in methanol was heated under reflux for 18 h before concentrating in vacuo. The residue was again dissolved in methanol (ca 5 ml) and heated at reflux for 3 hours, followed by evaporation to dryness in vacuo. This process was repeated once more and extensive drying gave a brown oil (270 mg) which was purified by column chromatography on silica gel (13 g) eluting with dichloromethane:ethanol:0.88 ammonia (150:8:1). This gave the title compound as an orange oil (124 mg, 53%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 h
  3. temperaturebefore cooling
  4. customquenching with dry methanol (2 ml)
  5. temperatureThe solution in methanol was heated
  6. temperatureunder reflux for 18 h
  7. concentrationbefore concentrating in vacuo
  8. dissolutionThe residue was again dissolved in methanol (ca 5 ml)
  9. temperatureheated
  10. temperatureat reflux for 3 hours
  11. customfollowed by evaporation to dryness in vacuo
  12. customextensive drying

Sources & evidence

ORD record
ord-ba1010f28228469c94090c59b03e0057
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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