Pyridine → HCID 54000323, compound

HRID 428308Notes

Reaction equation

HRID 428308 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]([C@H:27]([C@@H:29]([C@@H:31]([CH2:48][O:49][CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[O:32][CH2:33][C:34]1[CH:39]=[CH:38][C:37]([O:40]CC2C=CC=CC=2)=[CH:36][CH:35]=1)[OH:30])[OH:28])[O:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19]CC2C=CC=CC=2)=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1>CO.[Pd]>[CH2:1]([O:8][CH2:9][C@H:10]([C@H:27]([C@@H:29]([C@@H:31]([CH2:48][O:49][CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[O:32][CH2:33][C:34]1[CH:35]=[CH:36][C:37]([OH:40])=[CH:38][CH:39]=1)[OH:30])[OH:28])[O:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 1049PyridineHCID 54069036HCID 54069036, compound

Product 1

HCID 54000323HCID 54000323, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1,6-di-O-benzyl-2,5-di-O-(4-benzyloxybenzyl)-D-mannitol, obtained as in example 15, (97 mg, 0.10 mmol) in MeOH (1 mL), pyridine (8.0 mg, 0.1 mmol) and 5% palladium on charcoal (70 mg) was hydrogenated at normal pressure and room temperature for 1 h. The reaction mixture was filtered and concentrated in vacuo. Flash chromatography on silica gel eluting with 50% EtOAc in hexane afforded the title compound in 87% yield.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2eff1daff5c8428e95a1700c7abf39b8
Source dataset
uspto-grants-2001_11
Patent number
US06313177B1

Reaction notes

Loading…