Sodium borohydride → 1-(4-Benzyloxy-3-hydroxymethyl-phenyl)-2-(1,1-dimethyl-3-[1,2,4]triazol-1-yl-propylamino)-ethanol

HRID 1787846Notes

Reaction equation

HRID 1787846 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]([CH:19]([OH:32])[CH2:20][NH:21][C:22]([CH3:31])([CH3:30])[CH2:23][CH2:24][N:25]2[CH:29]=[N:28][CH:27]=[N:26]2)=[CH:15][C:10]=1[C:11](OC)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Ca+2].[Cl-].[BH4-].[Na+]>>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]([CH:19]([OH:32])[CH2:20][NH:21][C:22]([CH3:31])([CH3:30])[CH2:23][CH2:24][N:25]2[CH:29]=[N:28][CH:27]=[N:26]2)=[CH:15][C:10]=1[CH2:11][OH:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 68877359Methyl 2-benzyloxy-5-[2-[1,1-dimethyl-3-[1,2,4]triazol-1-yl-propylamino]-1-hydroxy-ethyl]-benzoate

Product 1

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

Procedure

7.6 g of methyl 2-benzyloxy-5-[2-[1,1-dimethyl-3-[1,2,4]triazol-1-yl-propylamino]-1-hydroxy-ethyl]-benzoate are reduced in an ethanolic calcium chloride solution with sodium borohydride as described for Example 1c. The product is obtained as a colourless oil after purification by column chromatography (CHCl3/MeOH/NH3=90/10/0.5). Yield: 6 g (84%).

Workup

  1. customThe product is obtained as a colourless oil
  2. customafter purification by column chromatography (CHCl3/MeOH/NH3=90/10/0.5)

Sources & evidence

ORD record
ord-6a530b77776841f8a59965f50e2d8619
Source dataset
uspto-grants-2009_03
Patent number
US07511067B2

Reaction notes

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