[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7](=[O:10])[CH2:8]Br)=[CH:5][CH:4]=1)#[N:2].[CH:13]12[CH2:21][CH:17]([CH2:18][NH:19][CH2:20]1)[CH2:16][N:15]([C:22]([O:24][CH:25]([CH3:27])[CH3:26])=[O:23])[CH2:14]2.[BH4-].[Na+]>CC#N>[C:1]([C:3]1[CH:12]=[CH:11][C:6]([CH:7]([OH:10])[CH2:8][N:19]2[CH2:20][CH:13]3[CH2:21][CH:17]([CH2:16][N:15]([C:22]([O:24][CH:25]([CH3:27])[CH3:26])=[O:23])[CH2:14]3)[CH2:18]2)=[CH:5][CH:4]=1)#[N:2]4-Cyanophenacyl bromide (225 mg; 1 mmol) was added to a stirred solution of iso-propyl 3,7-diazabicyclo[3.3.1]nonane-3-carboxylate (from step (iv) above; 212 mg; 1 mmol) in MeCN (2 mL). After stirring for 15 min at 0° C., NaBH4 (40 mg; 1 mmol) was added, and the reaction was allowed to warm to rt over 45 minutes. The reaction mixture was concentrated, dissolved in CH2Cl2 and washed with NaHCO3 (aq.) and brine. The organic layer was separated, dried and concentrated to give an oil which was purified using column chromatography (hexane:EtOAc:IPA; 50:49:1) to give the sub-title compound in 35% yield.
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