HCID 131716986, compound → HCID 67924778, compound

HRID 2248953Notes

Reaction equation

HRID 2248953 reaction equation
C([O:8][C:9]1[CH:17]=[C:16]([O:18]CC2C=CC=CC=2)[CH:15]=[C:14]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C@@H:31]([OH:38])[CH2:32][CH2:33][CH2:34][C@@H:35]([OH:37])[CH3:36])[C:10]=1[C:11]([OH:13])=[O:12])C1C=CC=CC=1.[H][H]>[Pd].C(O)C>[OH:8][C:9]1[CH:17]=[C:16]([OH:18])[CH:15]=[C:14]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C@@H:31]([OH:38])[CH2:32][CH2:33][CH2:34][C@@H:35]([OH:37])[CH3:36])[C:10]=1[C:11]([OH:13])=[O:12]

Participants

5

Reactant 2

HCID 131716986HCID 131716986, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67924778HCID 67924778, compoundYield 89.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 6.00 g of compound B from Example II and 6.03 g of 5% palladium on charcoal in 100 mL of ethanol was treated with hydrogen gas at a constant pressure of 50 psi for 5.0 hours at room temperature. The reaction was filtered through celite and concentrated under reduced pressure to provide 3.52 g of crude product. Recrystallization from aqueous ethanol furnished material with the following characteristics: mp 116°-8° C.; IR (KBr) 2993, 2860, 1660, 1540, 1225, 849 cm-1 ; 1H-NMR (DMSO-d6) δ 1.07 (d), 1.35 (brm), 6.11 (s), 6.18 (s), 7.00 (br); 13C-NMR (DMSO) δ 21.65, 23.57, 25.09, 29.36, 31.39, 35.40, 43.64, 65.88, 69.64, 100.55, 104.84, 110.04, 147.31, 161.58, 172.65.

Workup

  1. filtrationThe reaction was filtered through celite and
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-74ccdaae545e4baa8cf8285f23961681
Source dataset
uspto-grants-1991_08
Patent number
US05041610

Reaction notes

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