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

HRID 542974Notes

Reaction equation

HRID 542974 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-e2bc2d8740504923bb08c1d57e8fe3db
Source dataset
uspto-grants-1987_04
Patent number
US04659818

Reaction notes

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