Sodium borohydride → N-[6-(2,4-difluorophenoxy)1-hydroxy-5-indanyl]methanesulfonamide

HRID 1583913Notes

Reaction equation

HRID 1583913 reaction equation
[F:1][C:2]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:3]=1[O:4][C:5]1[CH:13]=[C:12]2[C:8]([CH:9](C3C=CC=CC=3)[CH2:10][C:11]2=[O:14])=[CH:7][C:6]=1[NH:21][S:22]([CH3:25])(=[O:24])=[O:23].[BH4-].[Na+]>CO.[OH-].[Na+]>[F:1][C:2]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:3]=1[O:4][C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][CH:11]2[OH:14])=[CH:7][C:6]=1[NH:21][S:22]([CH3:25])(=[O:24])=[O:23]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 13208965HCID 13208965, compound

Product 1

HCID 13084202N-[6-(2,4-difluorophenoxy)1-hydroxy-5-indanyl]methanesulfonamideYield 96.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

2.13 g of 6-(2,4-difluorophenoxy)-5-methylsulfonylamino-3-phenyl-1-indanone is dissolved in 20 ml of methanol and 5.5 ml of 1N sodium hydroxide solution. At 0° C., 400 mg of sodium borohydride is added to the mixture. After 16 hours at 20° C., the mixture is concentrated, combined with water, neutralized with 1N sulfuric acid, and vacuum-filtered, thus obtaining 1.7 g of N-[6-(2,4-difluorophenoxy)1-hydroxy-5-indanyl]methanesulfonamide, mp 119° C.

Workup

  1. concentrationthe mixture is concentrated
  2. filtrationvacuum-filtered

Sources & evidence

ORD record
ord-5f6a7e29d71c4ea981fbe098691fe2d7
Source dataset
uspto-grants-1985_11
Patent number
US04555406

Reaction notes

Loading…