HCID 89524690, compound → HCID 89533825, compound

Participants

Reaction Steps

To a flask was added 7-((tert-butoxycarbonyl)amino)-5,6,7,8-tetrahydro-naphthalene-1-carboxylic acid (20-1) (2.02 g, 6.93 mmol), then anhydrous THF (20 mL). The reaction mixture was cooled to 0 C (ice water bath) while stirring under an atmosphere of nitrogen. Then a 1M solution of BORANE TETRAHYDROFURAN COMPLEX (30 mL, 30.0 mmol) was added dropwise while stirring. The reaction mixture was stirred at 0 C for 1.5 hours. Followed by LC/MS. The reaction mixture was then uncapped (always at 0 C), then quenched by dropwise addition of saturated NH4Cl (lots of bubbling/gas evolution). The reaction mixture was then warmed to room temperature, then suspended in EtOAc, separated, the organics were then washed with saturated NaHCO3, then H2O, then brine; dried over Na2SO4, filtered & concentrated. The resulting residue was purified by silica gel chromatography (0-50% EtOAc/Hex; 80 g ISCO); desired fractions concentrated to yield tert-butyl (8-(hydroxymethyl)-1,2,3,4-tetrahydronaphthalen-2-yl)carbamate (20-2).

Provenance & Evidence