MeOH tetrahydrofuran → HCID 71077046, compound

HRID 2206814Notes

Reaction equation

HRID 2206814 reaction equation
Cl[C:2]1[C:10]2OC[CH:7](OC)[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.[CH2:62]1[CH2:66][O:65][CH2:64][CH2:63]1.CO>[Pd]>[CH:10]1([C:2]2[C:66]3[O:65][CH2:64][CH2:63][C:62]=3[C:5]([C@H:13]3[C@H:18]([OH:19])[C@@H:17]([OH:27])[C@H:16]([OH:35])[C@@H:15]([CH2:43][OH:44])[O:14]3)=[CH:4][C:3]=2[CH2:52][C:53]2[CH:54]=[CH:55][C:56]([O:59][CH2:60][CH3:61])=[CH:57][CH:58]=2)[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 21899815MeOH tetrahydrofuranHCID 86714101HCID 86714101, compound

Product 1

HCID 71077046HCID 71077046, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

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 (102 mg, 0.125 mmol) in THF/MeOH (4 mL/2 mL) was added 10% Pd/C (10 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 (17 mg, 29%) 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-322173cf379e4c97a71ae3560b58b4fc
Source dataset
uspto-grants-2016_06
Patent number
US09371303B2

Reaction notes

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