C(O[C:4]([N:6]1[CH2:18][C@H:17]2[C@H:9]([CH2:10][C:11]3[C:16]2=[CH:15][C:14]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][C:12]=3[CH3:25])[CH2:8][CH2:7]1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:4][N:6]1[CH2:18][C@H:17]2[C@H:9]([CH2:10][C:11]3[C:16]2=[CH:15][C:14]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][C:12]=3[CH3:25])[CH2:8][CH2:7]1To a solution of cis-8-methyl-6-phenyl-1,2,4,4a,9,9a-hexahydro-3-aza-fluorene-3-carboxylic acid ethyl ester (20 mg, 0.060 mmol) in THF (1.0 mL) was added LiAlH4 (4.5 mg, 0.12 mmol) under Ar. The reaction mixture was stirred at 20° C. for 2 h then refluxed for 4 h. The reaction was cooled to 20° C. and quenched by addition of H2O and 1M NaOH. The quenched reaction mixture was extracted with CH2Cl2. The combined organic solution was dried over MgSO4, filtered and concentrated in vacuo. The residue was chromatographed in silica gel column (Hex/EtOAc 1/1) to obtain the title compound (10 mg, 0.036 mmol): MS (ES) 278.2 (M+H).
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