Cyclohexene → HCID 59444173, compound

HRID 1968998Notes

Reaction equation

HRID 1968998 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-5ef897a59068459c8af485e400552c8a
Source dataset
uspto-grants-2013_04
Patent number
US08426443B2

Reaction notes

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