Nitrogen → HCID 57079368, compound

HRID 234732Notes

Reaction equation

HRID 234732 reaction equation
[CH3:1][C:2]1[C@@H:3]2[C@@H:19]([C@:20]3([CH3:28])[C:25]([CH:26]=1)=[CH:24][C:23](=[O:27])[CH2:22][CH2:21]3)[CH2:18][CH2:17][C@@:16]1([CH3:29])[C@H:4]2[CH2:5][CH2:6][C@@H:7]1[C@H:8]([CH3:15])[CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12].C1CCCCC=1.N#N>[Pd].C(O)C>[CH3:1][C@H:2]1[CH2:26][C:25]2[C@:20]([CH3:28])([CH2:21][CH2:22][C:23](=[O:27])[CH:24]=2)[C@@H:19]2[C@@H:3]1[C@H:4]1[C@:16]([CH3:29])([CH2:17][CH2:18]2)[C@@H:7]([C@H:8]([CH3:15])[CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH2:6][CH2:5]1

Participants

6

Reactant 3

HCID 947NitrogenHCID 8079CyclohexeneHCID 54273405HCID 54273405, compound

Product 1

HCID 57079368HCID 57079368, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of methyl 7-methyl-3-oxochola-4,6-dien-24-oate (9) (0.62 g, 1.56 mmoles), 5% palladium on carbon (72 mg), 1,8diazobicyclo-[5.4.0]undec-7-ene (15 gl), cyclohexene (4.9 ml) and ethanol (3.6 ml) was heated under reflux in an N2 for 6 hrs. The cooled mixture was filtered, and the catalyst washed with ethanol (4 times). The combined filtrate and washes were evaporated in vacuo. The residue was dissolved in EtOAc (30 ml), washed with 0.5M HCl, H2O, saturated brine and dried (MgSO4). Evaporation in vacuo gave 0.62 g of pure 10 as a pale yellow syrup. NMR (CDCl3): δ0.71 (s, 3H, 18-Me); 0.94 (d, 3H, 20-Me); 1.05 (d, 3H, 7-Me); 1.15 (s, 3H, 19-Me); 3.66 (s, 3H, CO2Me); 5.70 (s, 1H, 4-H).

Workup

  1. temperaturewas heated
  2. filtrationThe cooled mixture was filtered
  3. washthe catalyst washed with ethanol (4 times)
  4. customThe combined filtrate and washes were evaporated in vacuo
  5. dissolutionThe residue was dissolved in EtOAc (30 ml)
  6. washwashed with 0.5M HCl, H2O, saturated brine
  7. dry with materialdried (MgSO4)
  8. customEvaporation in vacuo

Sources & evidence

ORD record
ord-94480eae1cc1438ea289a51c587d2057
Source dataset
uspto-grants-1997_01
Patent number
US05595996

Reaction notes

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