Lithium borohydride → HCID 23000593, compound

Participants

Reaction Conditions

Reaction Steps

Into a stirred solution of 2-(tert-butoxycarbonyl)-7-chloro-3,4-dihydro-2H-isoquinolin-1-one (18.4 g, 64.38 mMol) in 50 mL of anhydrous tetrahydrofuran under inert atmosphere at 0° C. was added 2.0M LiBH4 in tetrahydrofuran (64.38 mL, 128.76 mMol, 2 eq). This was stirred at 0° C. for 1.5 hours, quenched with saturated ammonium chloride solution, then partitioned between ethyl acetate and water. The organics were dried(Na2SO4) and concentrated in vacuo. This afforded 2-(tert-butoxycarbonylaminoethyl)-5-chlorobenzyl alcohol as a clear colorless oil (hplc rt=3.21 min, method A; mass spec m/z=286.2).

Provenance & Evidence