Aluminium lithium hydride → (S)-benzyl 5-(3-(hydroxymethyl)-5-(trifluoromethyl)benzyl)-2,3-dihydro-1H-inden-2-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

To (S)-methyl 3-((2-(benzyloxycarbonylamino)-2,3-dihydro-1H-inden-5-yl)methyl)-5-(trifluoromethyl)benzoate (2.90 mmol, 1.4 g) at 0° C. in THF (29.0 mL) under an argon atmosphere was added Lithium aluminium hydride in THF (2.90 mmol, 2.90 mL) dropwise. The reaction was left to stir for 1.5 hrs at 0° C. The reaction was quenched with MeOH before the addition of 5N HCl (aq) to adjust the pH to 3. The reaction mix was diluted with DCM before washing with water (×1) followed by brine (×1). The DCM layer was dried over MgSO4 before removing the solvent in vacuo to give the product as a clear glassy solid (1.34 g, 102%). MS (ESI): m/z [M+H]+ 456.1

Provenance & Evidence