Water → HCID 131725217, compound

HRID 1063945Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11](C2C=C(Cl)C=CC=2Cl)[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>[CH3:18][C@@H:12]([NH:11][S:8]([C:5]1[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1)(=[O:10])=[O:9])[CH2:13][CH2:14][NH2:15]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4-chloro-N-(2,5-dichlorophenyl)-N-[(R)-1-methyl-3-azidopropyl]benzenesulfonamide (0.941 g, 2.16 mmol) in THF (21 mL) was added lithium aluminum hydride (4.33 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 0.165 mL of water, 0.165 mL of 15% sodium hydroxide solution, and 0.493 mL of water. The mixture was filtered and concentrated under reduced pressure. Silica gel chromatography (3:10 ethyl acetate:hexanes) of the concentrate afforded 0.748 g of 4-chloro-N-2,5-dichlorophenyl)-N-[(R)-1-methyl-3-aminopropyl]benzenesulfonamide as a light brown oil in 85% yield.

Workup

filtrationThe mixture was filtered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-94b602c682184784aaf127f9ded932b2
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06967196B1

Reaction notes

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