HCID 11955331, compound → HCID 11955333, compound

HRID 9240Notes

Reaction equation

HRID 9240 reaction equation
[CH3:1][O:2][C:3](=[O:31])[CH2:4][O:5][CH2:6][C:7]#[C:8][CH2:9][C@H:10]1[C@H:14]([Cl:15])[CH2:13][C@@H:12]([OH:16])[C@@H:11]1[C:17]1[CH:22]=[CH:21][C:20]([CH:23]([CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[OH:24])=[CH:19][CH:18]=1>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3](=[O:31])[CH2:4][O:5][CH2:6][CH2:7][CH2:8][CH2:9][C@H:10]1[C@H:14]([Cl:15])[CH2:13][C@@H:12]([OH:16])[C@@H:11]1[C:17]1[CH:22]=[CH:21][C:20]([CH:23]([CH:25]2[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]2)[OH:24])=[CH:19][CH:18]=1

Participants

4

Reactant 1

HCID 11955331HCID 11955331, compound

Product 1

HCID 11955333HCID 11955333, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 10-6 (11 mg, 0.024 mmol) and 5% Pd/C (6 mg, 0.003 mmol) in ethyl acetate (1 mL) was stirred under 1 atm H2 (balloon) for 18 h. The mixture was filtered and evaporated. The residue was purified by preparative TLC on silica gel (45% ethyl acetate/hexanes) to give 11-3 (8 mg, 0.018 mmol, 75%).

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated
  3. customThe residue was purified by preparative TLC on silica gel (45% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-c426a0ed2b1a44ed82fd530164038e55
Source dataset
uspto-grants-2006_08
Patent number
US07091231B2

Reaction notes

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