Cyclohexene → HCID 59444173, compound

HRID 2060044Notes

Reaction equation

HRID 2060044 reaction equation
[CH3:1][C:2]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([N+:14]([O-])=O)[CH:8]=2)[O:6][CH2:5][CH2:4][O:3]1.C1CCCCC=1>[Pd].C(O)C>[NH2:14][C:9]1[CH:8]=[C:7]([C:2]2([CH3:1])[O:3][CH2:4][CH2:5][O:6]2)[CH:12]=[CH:11][C:10]=1[OH:13]

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 190269674-(2-Methyl-1,3-dioxolan-2-yl)-2-nitrophenol

Product 1

HCID 59444173HCID 59444173, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A stirred mixture of 4-(2-methyl-1,3-dioxolan-2-yl)-2-nitrophenol D129 (2.40 g, 10.66 mmol), cyclohexene (4.38 g, 53.3 mmol) and 10% palladium on carbon (0.227 g, 0.213 mmol) in ethanol (75 mL) was heated to reflux for 6 hr under argon. The mixture was cooled to rt and the catalyst was removed by filtration through celite. The filtrate was concentrated to dryness in vacuo and the reside dissolved in 10% MeOH in DCM (20 mL) and passed through a SCX-2 cartridge (25 g) which was then eluted with further 10% MeOH in DCM to wash through any unreacted starting material and then with 2M ammonia in MeOH. The basic eluate was concentrated under vacuum to give the title compound as a yellow-brown solid (1.58 g, 76%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 6 hr under argon
  3. customthe catalyst was removed by filtration through celite
  4. concentrationThe filtrate was concentrated to dryness in vacuo
  5. dissolutionthe reside dissolved in 10% MeOH in DCM (20 mL)
  6. washwas then eluted with further 10% MeOH in DCM
  7. washto wash through
  8. concentrationThe basic eluate was concentrated under vacuum

Sources & evidence

ORD record
ord-06666e0358c94be1b9ac825173e826a2
Source dataset
uspto-grants-2012_10
Patent number
US08278328B2

Reaction notes

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