HCID 15651830, compound → HCID 15651831, compound

HRID 654571Notes

Reaction equation

HRID 654571 reaction equation
[CH2:1]([C:13]1([CH2:29][C:30]2[CH:35]=[C:34]([O:36]CC3C=CC=CC=3)[CH:33]=[CH:32][C:31]=2[O:44]CC2C=CC=CC=2)[CH2:26][O:25][CH2:24][CH2:23][O:22][CH2:21][C:20]([CH3:28])([CH3:27])[CH2:19][O:18][CH2:17][CH2:16][O:15][CH2:14]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]>C(OCC)(=O)C.CO.[Pd]>[CH2:1]([C:13]1([CH2:29][C:30]2[CH:35]=[C:34]([OH:36])[CH:33]=[CH:32][C:31]=2[OH:44])[CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][C:20]([CH3:27])([CH3:28])[CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 1

HCID 15651830HCID 15651830, compound

Product 1

HCID 15651831HCID 15651831, compoundYield 108%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 15.8 g (22.5 mmol) of Compound 5 in 20 mL of ethyl acetate and 20 mL of methanol was mixed with 0.4 g of palladium-on-carbon in a parr flask under a nitrogen atmosphere. The mixture was reacted at 50-60° C. under 50 psi H2 for 4 hours. After cooling, the product was filtered through Celite diatomaceous earth and the solvent removed to yield 12.7 g of impure product (Compound 6).

Workup

  1. customThe mixture was reacted at 50-60° C. under 50 psi H2 for 4 hours
  2. temperatureAfter cooling
  3. filtrationthe product was filtered through Celite diatomaceous earth
  4. customthe solvent removed

Sources & evidence

ORD record
ord-91d9856542a74a95afbde1544372e17a
Source dataset
uspto-grants-1992_07
Patent number
US05132436

Reaction notes

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