[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([CH2:9][CH:10]1[O:24][CH:13]2[O:14][CH:15]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[CH2:16][CH:12]2[CH2:11]1)#[N:8].O.[OH-].[Na+]>C1COCC1>[NH2:8][CH2:7][CH2:9][CH:10]1[O:24][CH:13]2[O:14][CH:15]([C:17]3[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=3)[CH2:16][CH:12]2[CH2:11]1Lithium aluminium hydride (92 mg, 2.5 mmol) was added to a stirred solution of 2-(cyanomethyl)-5-(4-fluorophenyl)hexahydrofuro[2,3-b]furan (300 mg, 1.2 mmol) in dry THF. The reaction mixture was stirred overnight and water (0.9 ml), 15% sodium hydroxide (0.9 ml) and water (2.7 ml) are added in succession. The white percipitate was filtered off and the solvent removed under reduced pressure to give crude 5-(2-aminoethyl)-2-(4-fluorophenyl)hexahydrofuro[2,3-b]furan which is used directly in the next step.
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