1-(4-Benzyloxy-3-hydroxymethyl-phenyl)-2-(1,1-dimethyl-3-[1,2,4]triazol-1-yl-propylamino)-ethanol → 4-[2-(1,1-Dimethyl-3-[1,2,4]triazol-1-yl-propylamino)-1-hydroxy-ethyl]-2-hydroxymethyl-phenol

HRID 1787847Notes

Reaction equation

HRID 1787847 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([OH:28])[CH2:16][NH:17][C:18]([CH3:27])([CH3:26])[CH2:19][CH2:20][N:21]2[CH:25]=[N:24][CH:23]=[N:22]2)=[CH:11][C:10]=1[CH2:29][OH:30])C1C=CC=CC=1>[Pd].CO>[CH3:27][C:18]([NH:17][CH2:16][CH:15]([C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([CH2:29][OH:30])[CH:11]=1)[OH:28])([CH3:26])[CH2:19][CH2:20][N:21]1[CH:25]=[N:24][CH:23]=[N:22]1

Participants

4

Reactant 1

HCID 688781131-(4-Benzyloxy-3-hydroxymethyl-phenyl)-2-(1,1-dimethyl-3-[1,2,4]triazol-1-yl-propylamino)-ethanol

Product 1

HCID 576025214-[2-(1,1-Dimethyl-3-[1,2,4]triazol-1-yl-propylamino)-1-hydroxy-ethyl]-2-hydroxymethyl-phenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The debenzylation of 6 g of 1-(4-benzyloxy-3-hydroxymethyl-phenyl)-2-(1,1-dimethyl-3-[1,2,4]triazol-1-yl-propylamino)-ethanol is carried out hydrogenolytically with 1 g of palladium on charcoal (5%) in 100 mL methanol. After the catalyst has been removed by suction filtering and the filtrate has been evaporated down the residue is dissolved in 20 mL 90% ethanol, combined with sulphuric acid and seeded. The precipitated product is filtered off and washed. Yield: 3 g (55%, hemisulphate); m.p.=177-180° C.

Workup

  1. customAfter the catalyst has been removed by suction
  2. filtrationfiltering
  3. customthe filtrate has been evaporated down the residue
  4. dissolutionis dissolved in 20 mL 90% ethanol
  5. filtrationThe precipitated product is filtered off
  6. washwashed

Sources & evidence

ORD record
ord-f373ea10a6a84604b61c0f16d566114d
Source dataset
uspto-grants-2009_03
Patent number
US07511067B2

Reaction notes

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