Aluminium lithium hydride → (R)-N-(5-(hydroxymethyl)-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide
Reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[CH2:10][C@@H:9]([NH:14][S:15]([CH:18]([CH3:20])[CH3:19])(=[O:17])=[O:16])[CH2:8]2)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[OH:2][CH2:3][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[CH2:10][C@@H:9]([NH:14][S:15]([CH:18]([CH3:20])[CH3:19])(=[O:17])=[O:16])[CH2:8]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
(R)-methyl-2-(1-methylethylsulfonamido)-2,3-dihydro-1H-indene-5-carboxylate (7.13 mmol, 2.12 g) was dissolved in dry THF (100 mL) and the vessel purged with nitrogen. Lithium aluminium hydride (1M, 14.3 mmol, 14.3 mL) was added dropwise and stirring continued for 20 min. The mixture was quenched by addition of methanol followed by water and 1N HCl before concentration to remove organics. The residue was partitioned between EtOAc/1N HCl. and the phases mixed and separated. The aqueous layer was further extracted with EtOAc (×2) Combined organics washed with brine and concentrated before purification on silica eluting with 1% MeOH/DCM to give (R)—N-(5-(hydroxymethyl)-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide as a light coloured solid (1.76 g, 92%). 1H NMR (400 MHz, CDCl3) δ 1.40 (d, 6H) 1.60 (bs, 1H) 2.90 (m, 2H) 3.18 (sept, 1H) 3.32 (m, 2H) 4.19-4.33 (m, 2H) 4.66 (s, 2H) 7.20 (m, 2H) 7.26 (m, 1H)