Sodium borohydride → N-[3-(2-Amino-1-hydroxyethyl)-4-fluorophenyl]methanesulfonamide

HRID 2379190Notes

Reaction equation

HRID 2379190 reaction equation
Cl.[NH2:2][CH2:3][C:4]([C:6]1[CH:7]=[C:8]([CH:14]=[CH:15][C:16]=1[F:17])[NH:9][S:10]([CH3:13])(=[O:12])=[O:11])=[O:5].[BH4-].[Na+]>CO>[NH2:2][CH2:3][CH:4]([C:6]1[CH:7]=[C:8]([CH:14]=[CH:15][C:16]=1[F:17])[NH:9][S:10]([CH3:13])(=[O:11])=[O:12])[OH:5]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 18958065HCID 18958065, compound

Product 1

HCID 9838761N-[3-(2-Amino-1-hydroxyethyl)-4-fluorophenyl]methanesulfonamideYield 91.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3'-(2-Aminoacetyl)-4'-fluoromethanesulfonanilide hydrochloride (3 g) was dissolved in 30 ml of methanol, 0.20 g of sodium borohydride was added at 0°-5° C. and the mixture was made to react at the same temperature for 1 hour. The solvent was evaporated and the residue was made into free base using ion exchange resin (Dowex 50W X2), concentrated to dryness and the residue was recrystallized from methanol to give 2.4 g of (±)-3'-(2-amino-1-hydroxyethyl)-4'-fluoromethanesulfonanilide, m.p. 176°-179° C.

Workup

  1. customto react at the same temperature for 1 hour
  2. customThe solvent was evaporated
  3. concentrationconcentrated to dryness
  4. customthe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-36d75a62a53042c990fbac768beb8bc6
Source dataset
uspto-grants-1994_11
Patent number
US05360822

Reaction notes

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