HCID 86714095, compound → HCID 78002440, compound

HRID 576435Notes

Reaction equation

HRID 576435 reaction equation
[Cl:1][C:2]1[C:7]2[CH:8]([CH3:11])[CH2:9][O:10][C:6]=2[C:5]([CH:12]2[C@H:17]([O:18]CC3C=CC=CC=3)[C@@H:16]([O:26]CC3C=CC=CC=3)[C@H:15]([O:34]CC3C=CC=CC=3)[C@@H:14]([CH2:42][O:43]CC3C=CC=CC=3)[O:13]2)=[CH:4][C:3]=1[CH2:51][C:52]1[CH:57]=[CH:56][C:55]([O:58][CH2:59][CH3:60])=[CH:54][CH:53]=1>C1COCC1.CO.[Pd]>[Cl:1][C:2]1[C:7]2[CH:8]([CH3:11])[CH2:9][O:10][C:6]=2[C:5]([CH:12]2[CH:17]([OH:18])[CH:16]([OH:26])[CH:15]([OH:34])[CH:14]([CH2:42][OH:43])[O:13]2)=[CH:4][C:3]=1[CH2:51][C:52]1[CH:53]=[CH:54][C:55]([O:58][CH2:59][CH3:60])=[CH:56][CH:57]=1

Participants

4

Reactant 1

HCID 86714095HCID 86714095, compound

Product 1

HCID 78002440HCID 78002440, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 4-chloro-5-(4-ethoxybenzyl)-3-methyl-7-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)-2,3-dihydrobenzofuran (102 mg, 0.124 mmol) in THF/MeOH (4 mL/2 mL) was added 10% Pd/C (50 mg) at rt. The reaction mixture was stirred at r.t. for 15 hours under hydrogen and filtered off. The filtrate was concentrated in vacuo and the residue was purified using reverse phase preparative HPLC to provide the title compound (24 mg, 42%) as a white solid.

Workup

  1. filtrationfiltered off
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue was purified

Sources & evidence

ORD record
ord-f76be753d5f042969ffd96275080f0c9
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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