HCID 86714101, compound → HCID 71076935, compound

HRID 576440Notes

Reaction equation

HRID 576440 reaction equation
[Cl:1][C:2]1[C:10]2[O:9][CH2:8][CH:7]([O:11][CH3:12])[C:6]=2[C:5]([CH:13]2[C@H:18]([O:19]CC3C=CC=CC=3)[C@@H:17]([O:27]CC3C=CC=CC=3)[C@H:16]([O:35]CC3C=CC=CC=3)[C@@H:15]([CH2:43][O:44]CC3C=CC=CC=3)[O:14]2)=[CH:4][C:3]=1[CH2:52][C:53]1[CH:58]=[CH:57][C:56]([O:59][CH2:60][CH3:61])=[CH:55][CH:54]=1>C1COCC1.CO.[Pd]>[Cl:1][C:2]1[C:10]2[O:9][CH2:8][CH:7]([O:11][CH3:12])[C:6]=2[C:5]([C@H:13]2[C@H:18]([OH:19])[C@@H:17]([OH:27])[C@H:16]([OH:35])[C@@H:15]([CH2:43][OH:44])[O:14]2)=[CH:4][C:3]=1[CH2:52][C:53]1[CH:58]=[CH:57][C:56]([O:59][CH2:60][CH3:61])=[CH:55][CH:54]=1

Participants

4

Reactant 1

HCID 86714101HCID 86714101, compound

Product 1

HCID 71076935HCID 71076935, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 7-chloro-6-(4-ethoxybenzyl)-3-methoxy-4-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)-2,3-dihydrobenzofuran (124 mg, 0.147 mmol) in THF/MeOH (4 mL/2 mL) was added 10% Pd/C (12 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 (38 mg, 54%) 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-ea79707552b24e6c924713b9eb2e0385
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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