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

HRID 462549Notes

Reaction equation

HRID 462549 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13](=[O:19])[CH2:14][S:15]([CH3:18])(=[O:17])=[O:16])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[NH:9][CH3:10].[BH4-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[NH:9][CH3:10])[CH:13]([OH:19])[CH2:14][S:15]([CH3:18])(=[O:17])=[O:16]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 212809593',5'-Dimethoxy-4'-(methylamino)-2-(methylsulfonyl)-acetophenone

Product 1

HCID 538586323,5-Dimethoxy-4-(methylamino)-alpha-[(methylsulfonyl)-methyl]-benzyl alcohol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 31 g. of 3',5'-dimethoxy-4'-(methylamino)-2-(methylsulfonyl)-acetophenone and 16.3 g. of sodium borohydride in 600 ml. of ethanol was stirred at room temperature for 16 hours. The solution was diluted with 600 ml. of water and the alcohol was removed by distillation under vacuum. The crystals formed were filtered with suction, washed with water and dried, whereby there was obtained 3,5-dimethoxy-4-(methylamino)-α-[(methylsulfonyl)-methyl]-benzyl alcohol having a melting point of 141°-142° C.

Workup

  1. additionA suspension of 31 g
  2. additionThe solution was diluted with 600 ml
  3. customof water and the alcohol was removed by distillation under vacuum
  4. customThe crystals formed
  5. filtrationwere filtered with suction
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-f6df38a19eae414b8ad9caba5945785d
Source dataset
uspto-grants-1985_05
Patent number
US04515948

Reaction notes

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