CC(C)(C)CC([N:6]1[CH2:10][C@H:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C@@H:8](C=O)[CH2:7]1)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:35]CCCl>C(Cl)Cl>[ClH:35].[C:11]1([CH:9]2[CH2:10][NH:6][CH2:7][CH2:8]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1To 89 mg (0.35 mmol) of 1-isopropyl-3-methyl-bicyclo[3.2.1]-1β,3,8-triaza-spiro[4.5]dodecan-2,4-dione in DCE (5 mL) was added 97 mg (0.35 mmol) of (3R,4S)-1-(3,3-dimethyl-butyryl)-4-phenyl-pyrrolidine-3-carbaldehyde in DCE (5 mL) and stirred for 2 hours at room temperature. Sodium triacetoxyborohydride (113 mg, 0.53 mmol) was then added and the reaction mixture stirred overnight at room temperature. The reaction mixture was diluted with DCM, the organic layer washed with sodium bicarbonate, and then dried over sodium sulfate. The reaction mixture was filtered, purified by semi-preparative HPLC (Method B) and lyophilized to give (3S,4S)-1-(3,3-dimethyl-butyryl)-3-[1-isopropyl-3-methyl-bicyclo[3.2.1]-2,4-dioxo-1β,3,8-triaza-spiro[4.5]dodec-8-ylmethyl]-4-phenyl-pyrrolidine hydrochloride (16 mg, 8%).
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