Sodium borohydride → 4-Amino-3,5-dimethyl-alpha-[(methylsulfonyl)-methyl]-benzyl alcohol

HRID 462556Notes

Reaction equation

HRID 462556 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:9](=[O:15])[CH2:10][S:11]([CH3:14])(=[O:13])=[O:12])=[CH:4][C:3]=1[CH3:16].[BH4-].[Na+]>>[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH:9]([OH:15])[CH2:10][S:11]([CH3:14])(=[O:13])=[O:12])=[CH:4][C:3]=1[CH3:16]

Participants

3

Reactant 2

HCID 4311764Sodium borohydrideHCID 212810124'-Amino-3',5'-dimethyl-2-(methylsulfonyl)-acetophenone

Product 1

HCID 538208514-Amino-3,5-dimethyl-alpha-[(methylsulfonyl)-methyl]-benzyl alcohol

Procedure

A suspension of 16.5 g. of 4'-amino-3',5'-dimethyl-2-(methylsulfonyl)-acetophenone and 10.6 g. of sodium borohydride in 500 ml. of alcohol was stirred at room temperature for 20 hours, resulting in a solution. After the addition of 500 ml. of water, the alcohol was evaporated under vacuum and the mixture was extracted with two 1 liter portions of ethyl acetate. The ethyl acetate extract was washed with two 500 ml. portions of water, dried over magnesium sulfate and evaporated under vacuum. After crystallization of the residue from ether, there was obtained 4-amino-3,5-dimethyl-α-[(methylsulfonyl)-methyl]-benzyl alcohol having a melting point of 146°-148° C.

Workup

  1. additionA suspension of 16.5 g
  2. customresulting in a solution
  3. additionAfter the addition of 500 ml
  4. customof water, the alcohol was evaporated under vacuum
  5. extractionthe mixture was extracted with two 1 liter portions of ethyl acetate
  6. extractionThe ethyl acetate extract
  7. washwas washed with two 500 ml
  8. dry with materialportions of water, dried over magnesium sulfate
  9. customevaporated under vacuum
  10. customAfter crystallization of the residue from ether

Sources & evidence

ORD record
ord-aea207f1247a439f8543dac747a6b818
Source dataset
uspto-grants-1985_05
Patent number
US04515948

Reaction notes

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