1: 1.) NBS; 2.) triethylamine / 1.) DMF, -20 deg C, 1 h, 0 deg C, 30 min; 2.) DMF, Et2O, RT, 18 h 2: 80 percent / boric acid, H2 / Raney Ni (W-2) / ethanol; H2O / 12 h / 760 Torr / Ambient temperature View Scheme

1: 95 percent / aq. hydroxylamine hydrochloride / ethanol / 11.5 h / Ambient temperature 2: 1.) NBS; 2.) triethylamine / 1.) DMF, -20 deg C, 1 h, 0 deg C, 30 min; 2.) DMF, Et2O, RT, 18 h 3: 80 percent / boric acid, H2 / Raney Ni (W-2) / ethanol; H2O / 12 h / 760 Torr / Ambient temperature View Scheme

1: 1.) NBS; 2.) triethylamine / 1.) DMF, -20 deg C, 1 h, 0 deg C, 30 min; 2.) DMF, Et2O, RT, 18 h 2: 80 percent / boric acid, H2 / Raney Ni (W-2) / ethanol; H2O / 12 h / 760 Torr / Ambient temperature View Scheme

N,N,N',N',N'',N''-hexamethylphosphoric triamide; n-butyllithium; sodium hydride 1.) THF, r.t., 30 min; 2.) THF, hexane, (-40)-(-30) deg C, 30 min; 3.) THF, hexane, -78 deg C, 1 h; Yield given. Multistep reaction;

Yield given. Multistep reaction. Yields of byproduct given;