[NH2:1][C:2]([CH2:9][CH3:10])([CH2:5][CH2:6][CH2:7][CH3:8])[CH2:3][OH:4].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH2:1][C@:2]([CH2:9][CH3:10])([CH2:5][CH2:6][CH2:7][CH3:8])[CH2:3][OH:4]The product from step (e) (20 g) was added to a 1M solution of lithium aluminium hydride (1.5 molar equivalents) in THF and the mixture reflexed for 3 hours, then stirred for 16 hours at room temperature. The mixture was cooled to about 0° C., then quenched with water and 1N aqu. NaOH added. The resulting solid was broken up with additional water and the suspension heated at 50° C. for 5 minutes, then cooled to room temperature, diethyl ether (100 ml) added and filtered. The filtrate was evaporated in vacuo to give the desired product as an oil (82% yield).
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