Water → HCID 54564987, compound

HRID 1063957Notes

Reaction equation

HRID 1063957 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=2[F:27])[C@H:12]([CH3:19])[CH2:13][CH2:14][CH2:15][N:16]=[N+]=[N-])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=2[F:27])[C@H:12]([CH3:19])[CH2:13][CH2:14][CH2:15][NH2:16])(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 53901294HCID 53901294, compound

Product 1

HCID 54564987HCID 54564987, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-chloro-N-(2,5-difluorophenyl)-N-[(R)-1-methyl-4-azidobutyl]benzene-sulfonamide (0.394 g, 0.949 mmol) in THF (10 mL) was added lithium aluminum hydride (1.90 mL, 1 M in THF) at 0° C. under nitrogen atmosphere. The resulting mixture was allowed to stir at 0° C. for 1 h and subsequently treated by successive dropwise addition of 0.072 mL of water, 0.072 mL of 15% sodium hydroxide solution, and 0.216 mL of water. The mixture was filtered and concentrated under reduced pressure. Silica gel chromatography (3:10 ethyl acetate:hexanes) of the concentrate afforded 0.329 g of 4-chloro-N-(2,5-difluorophenyl)-N-[(R)-1-methyl-4-aminobutyl]benzenesulfonamide as a light brown oil in 89% yield.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ebf0bef064a3424e8c50f81513f08c13
Source dataset
uspto-grants-2005_11
Patent number
US06967196B1

Reaction notes

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