Sodium borohydride → 2-Amino-alpha-(4-benzyloxy-2-methoxyphenyl)-5-chlorobenzyl alcohol

HRID 1419063

Reaction equation

HRID 1419063 reaction equation
[NH2:1][C:2]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:8][C:7]=1[O:20][CH3:21])=[O:5].[BH4-].[Na+]>CO>[NH2:1][C:2]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:3]=1[CH:4]([OH:5])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:8][C:7]=1[O:20][CH3:21]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 540054462-Amino-4'-benzyloxy-5-chloro-2'-methoxybenzophenone

Product 1

HCID 539319582-Amino-alpha-(4-benzyloxy-2-methoxyphenyl)-5-chlorobenzyl alcoholYield 94.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-amino-4'-benzyloxy-5-chloro-2'-methoxybenzophenone (10 g) in methanol (100 ml) was added sodium borohydride (1.4 g). After being stirred for 24 h, the mixture was concentrated in vacuo. The residue was diluted with water (200 ml) and extracted with ethyl acetate (300 ml). The extract was washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1-2:1) to give 2-amino-α-(4-benzyloxy-2-methoxyphenyl)-5-chlorobenzyl alcohol (9.5 g) as colorless crystals (mp=101°-103° C.).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. additionThe residue was diluted with water (200 ml)
  3. extractionextracted with ethyl acetate (300 ml)
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1-2:1)

Sources & evidence

ORD record
ord-75070c53359242d9beace80b12ceeca5
Source dataset
uspto-grants-1999_03
Patent number
US05885979

Linked notes

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