[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([N:12]2[CH2:21][CH2:20][CH:19]3[CH:14]([CH:15]([NH:22]C(=O)OC(C)(C)C)[CH2:16][CH2:17][CH2:18]3)[CH2:13]2)=O)=[CH:4][CH:3]=1.B.Cl>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][N:12]2[CH2:21][CH2:20][CH:19]3[CH:14]([CH:15]([NH2:22])[CH2:16][CH2:17][CH2:18]3)[CH2:13]2)=[CH:6][CH:7]=1A solution of tert-butyl {(4aSR,8SR,8aRS)-2-[3-(4-fluorophenyl)propanoyl]decahydroisoquinolin-8-yl}carbamate (220 mg, 544 μmol) in tetrahydrofuran (5 mL) was treated with a solution of borane in tetrahydrofuran (1.0 M; 1.0 mL, 1.0 mmol) and the mixture was heated at reflux for 3 hours. The mixture was cooled and treated with 1.0 N aqueous hydrochloric acid and then heated at reflux for 2 hours. The mixture was cooled again to room temperature and concentrated to provide a white solid. The white solid was partitioned between ethyl acetate and 2.0 N aqueous sodium hydroxide. The organic phase was separated, dried over magnesium sulfate and concentrated to provide a colorless oil (151 mg, 95%). 1H NMR (300 MHz, CDCl3) δ7.05 (m, 2H), 6.87 (m, 2H), 3.57 (t, J=6 Hz, 2H), 3.51 (t, J=7 Hz, 2H), 3.20 (m, 1H), 2.86 (m, 1H), 2.51 (m, 2H), 2.44 (broad s, 2H), 2.4-2.2 (m, 2H), 1.8-1.4 (m, 7H), 1.3-0.8 (m, 3H). Mass spec (ES+) m/z 291.3 (M+H+, 100%).
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