Cyclohexene → HCID 12082689, compound

HRID 494029Notes

Reaction equation

HRID 494029 reaction equation
C([N:8](CC1C=CC=CC=1)[C@@H:9]1[CH2:22][CH2:21][C@:20]2([O:23][CH3:24])[C@:11]34[CH2:27][CH2:26][N:25]([CH3:28])[C@@H:19]2[CH2:18][C:17]2[CH:16]=[CH:15][C:14]([OH:29])=[C:13]([O:30][C@@H:10]13)[C:12]4=2)C1C=CC=CC=1.C1CCCCC=1>[Pd].CO>[NH2:8][C@@H:9]1[CH2:22][CH2:21][C@:20]2([O:23][CH3:24])[C@:11]34[CH2:27][CH2:26][N:25]([CH3:28])[C@@H:19]2[CH2:18][C:17]2[CH:16]=[CH:15][C:14]([OH:29])=[C:13]([O:30][C@@H:10]13)[C:12]4=2

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 12082688HCID 12082688, compound

Product 1

HCID 12082689HCID 12082689, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of Compound 14 (1.02 g, 2.05 mmol), 10% Pd/C catalyst (0.52 g), cyclohexene (30 ml) and absolute MeOH (30 ml) were reflux heated for 16 hours under N2. Then the catalyst was filtered off and the filtrate evaporated. The residue (0.66 g of white foam resin) was crystallised out of i-PrOH/Et2O 1:1 (2 ml). Yield: 0.33 g (42%) of beige crystals: Fp>235-239° C.; IR (KBr): 3348 (OH) cm−1; 1H-NMR (CDCl3): 6.62 (d, J=8.0, 1 arom. H); 6.54 (d, J=8.0, 1 arom. H); 4.26 (d, J=7.0, H—C(5)); 3.22 (s, CH3O—C(14)); 2.36 (s, CH3N); Cl-MS: m/z 317 (M++1).

Workup

  1. temperaturewere reflux
  2. temperatureheated for 16 hours under N2
  3. filtrationThen the catalyst was filtered off
  4. customthe filtrate evaporated
  5. customThe residue (0.66 g of white foam resin) was crystallised out of i-PrOH/Et2O 1:1 (2 ml)
  6. customFp>235-239° C.

Sources & evidence

ORD record
ord-db2064881eeb4c82924b83d9586f5e9f
Source dataset
uspto-grants-2009_05
Patent number
US07538118B2

Reaction notes

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