Water → HCID 54293466, compound

HRID 1063959Notes

Reaction equation

HRID 1063959 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=2[F:26])[C@H:12]([CH3:18])[CH2:13][CH2:14][N:15]=[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:19]2[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=2[F:26])[C@H:12]([CH3:18])[CH2:13][CH2:14][NH2:15])(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 54491635HCID 54491635, compound

Product 1

HCID 54293466HCID 54293466, compoundYield 97%

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-3-azidopropyl]benzenesulfonamide (0.144 g, 3.59 mmol) in THF (35 mL) was added lithium aluminum hydride (7.16 mL, 1 M in THF) at 0° C. under nitrogen atmosphere. The resulting mixture was allowed to stir at 0° C. for 1 h w and subsequently treated by successive dropwise addition of 0.272 mL of water, 0.272 mL of 15% sodium hydroxide solution, and 0.816 mL of water. The mixture was concentrated under reduced pressure. Silica gel chromatography (3:10 ethyl acetate:hexanes) of the concentrate afforded 1.12 g of 4-chloro-N-(2,5-difluorophenyl)-N-[(R)-1-methyl-3-aminopropyl]benzenesulfonamide as a light brown oil in 97% yield.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-281c46a628ee4ad7901a53df5ff7f851
Source dataset
uspto-grants-2005_11
Patent number
US06967196B1

Reaction notes

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