[CH3:1][C:2]1([CH3:18])[CH2:16][C:6]2[N:7]=[C:8]([N:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[S:9][C:5]=2[C:4](=[O:17])[CH2:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1>[CH3:1][C:2]1([CH3:18])[CH2:16][C:6]2[N:7]=[C:8]([N:10]3[CH2:11][CH2:12][O:13][CH2:14][CH2:15]3)[S:9][C:5]=2[CH:4]([OH:17])[CH2:3]1To a stirred solution of Example 48 (0.13 g, 0.5 mmol) in THF (10 mL) at r.t. was added LiAlH4 (0.5 mL, 1M solution in THF, 0.5 mmol) dropwise. The reaction mixture was stirred at r.t. for 2 h and then poured into 10% NaOH solution (20 mL) and extracted with DCM (2×20 mL). The combined organic fractions were dried over MgSO4, filtered and the solvent removed by evaporation in vacuo. Purification by column chromatography gave the title compound (0.07 g, 52%) as a solid. δH (DMSO-d6) 5.23 (1H, d, J 6.5 Hz), 4.65 (1H, dt, J 8.1 and 6.7 Hz), 3.77-3.70 (4H, m), 3.39 (4H, m), 2.40-2.24 (2H, m), 1.84 (1H, dd, J 5.9 and 11.3 Hz), 1.48 (1H, dd, J 8.8 and 12.6 Hz), 1.09 (3H, s), 0.94 (3H, s). LCMS (ES+) 269.0 (M+H)+.
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