Aluminium lithium hydride → (S)-N-(5-(hydroxymethyl)-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide

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Reaction Steps

(S)-methyl-2-(1-methylethylsulfonamido)-2,3-dihydro-1H-indene-5-carboxylate (2.502 mmol, 744 mg) was dissolved in dry THF (20 mL) and was purged with nitrogen and cooled in an ice bath. Lithium aluminium hydride (7.51 mmol, 7.51 mL) was added dropwise and stirring continued at 0° C. for 10 min. The mixture was quenched by addition of methanol followed by 1:1 THF/water and 1N HCl before concentration to remove organics. The residue was partitioned between dichlormethane/1N HCl. and the phases mixed and separated. The aqueous layer was further extracted with DCM (×2) Combined organics washed with brine and concentrated before purification on silica eluting with 2% MeOH/DCM to give (S)—N-(5-(hydroxymethyl)-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide (0.692 g, 103%). 1H NMR (400 MHz, CDCl3) δ 1.39 (d, 6H) 1.71 (bt, 1H) 2.89 (m, 2H) 3.18 (sept, 1H) 3.30 (m, 2H) 4.28 (m, 1H) 4.41 (m, 1H) 4.66 (d, 2H) 7.18 (m, 2H) 7.24 (m, 1H)

Provenance & Evidence