[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][NH:11][C:12](=O)[CH3:13])=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][NH:11][CH2:12][CH3:13])=[CH:6][CH:7]=1The product of Step d (1.10 g, 5.63 mmol, 1 eq.) was dissolved in THF at 25° C. under N2 then 1.0M LAH in THF (22.54 mL, 22.50 mmol, 4 eq.) was added dropwise via an addition funnel over 10 minutes. After the addition was complete, refluxed for 1 hour. Worked up by carefully adding water (0.86 mL)(Caution—lots of foaming and gas evolution were observed) dropwise via an addition funnel followed by 1N NaOH (3.42 mL). Stirred 20 minutes then filtered off the solids. The filtrate was stripped to give 0.90 g of a colorless oil as product. MS (ESI) detects (M+H)+=182.
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