HCID 12397269, compound → HCID 12397272, compound

HRID 1606310Notes

Reaction equation

HRID 1606310 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]([CH2:17][NH:18][C:19]([CH3:22])([CH3:21])[CH3:20])[OH:16])=[N:13][CH:14]=1)C1C=CC=CC=1>[Pd].C(O)C>[C:19]([NH:18][CH2:17][CH:15]([C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][N:13]=1)[OH:16])([CH3:22])([CH3:20])[CH3:21]

Participants

4

Reactant 1

HCID 12397269HCID 12397269, compound

Product 1

HCID 12397272HCID 12397272, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 600 mg. (2 mmol) of 5-benzyloxy-α-(N-t-butylaminomethyl)-2-pyridinemethanol (liberated from the hydrochloride salt) in 100 ml. of ethanol is hydrogenated over 600 mg. of 10% palladium-on-carbon at 50 psi for 10 minutes. The catalyst is filtered and ethanol evaporated to dryness. The residue is recrystallized from ethanol to give α-(t-butylaminomethyl)-5-hydroxy-2-pyridinemethanol, m.p. 163°-165°C.

Workup

  1. filtrationThe catalyst is filtered
  2. customethanol evaporated to dryness
  3. customThe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-5e8da901665446a4943a26a00090d3b3
Source dataset
uspto-grants-1976_04
Patent number
US03952101

Reaction notes

Loading…