3,5-Bis(benzyloxy)-4-((tert-butyldimethylsilyloxy)methyl)pyridine → 4-((Tert-butyldimethylsilyloxy)methyl)pyridine-3,5-diol

HRID 1471732Notes

Reaction equation

HRID 1471732 reaction equation
C([O:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13]([O:24]CC2C=CC=CC=2)[C:14]=1[CH2:15][O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])C1C=CC=CC=1>CCOC(C)=O.CCO.[Pd]>[Si:17]([O:16][CH2:15][C:14]1[C:9]([OH:8])=[CH:10][N:11]=[CH:12][C:13]=1[OH:24])([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]

Participants

4

Reactant 1

HCID 866907743,5-Bis(benzyloxy)-4-((tert-butyldimethylsilyloxy)methyl)pyridine

Product 1

HCID 866907734-((Tert-butyldimethylsilyloxy)methyl)pyridine-3,5-diol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

To 3,5-bis(benzyloxy)-4-((tert-butyldimethylsilyloxy)methyl)pyridine (720 mg, 1.66 mmol, 1 eq.) in a mixture of EtOAc/EtOH (5/2, 28 mL) was added Pd/C (400.0 mg). The mixture was charged with H2 (60 psi), stirred at rt for 2 h, filtered, and concentrated to give 4-((tert-butyldimethylsilyloxy)methyl)pyridine-3,5-diol as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.54 (s, 2H), 4.91 (s, 2H), 0.73 (s, 9H), −0.00 (s, 6H). LRMS (M+H) m/z 256.1.

Workup

  1. additionThe mixture was charged with H2 (60 psi)
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ea18a894dcf7474b99e683301312d700
Source dataset
uspto-grants-2015_04
Patent number
US09012450B2

Reaction notes

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