Aluminium lithium hydride → 4-[4-(6-Fluoro-benzo[b]thiophen-3-yl)-[1,4]diazapan-1-yl]butylamine
반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]1[CH:9]=[CH:10][C:11]2[C:15]([N:16]3[CH2:22][CH2:21][CH2:20][N:19]([CH2:23][CH2:24][CH2:25][C:26]#[N:27])[CH2:18][CH2:17]3)=[CH:14][S:13][C:12]=2[CH:28]=1>C(OCC)C>[F:7][C:8]1[CH:9]=[CH:10][C:11]2[C:15]([N:16]3[CH2:22][CH2:21][CH2:20][N:19]([CH2:23][CH2:24][CH2:25][CH2:26][NH2:27])[CH2:18][CH2:17]3)=[CH:14][S:13][C:12]=2[CH:28]=1참가 물질
4
실험 절차
Add over 30 min, at room temperature, a solution of LiAlH4 in diethyl ether (1M, 72.5 mL) to a solution of 4-[4-(6-fluoro-benzo[b]thiophen-3-yl)-[1,4]diazapan-1-yl]butyronitrile (Example 5) (11.5 g, 36.2 mmol) in dry diethyl ether (200 mL). Heat the solution to reflux for 5 h. After that time, allow the solution to cool to room temperature and carefully quench the reaction with water and aqueous sodium hydroxide solution. Separate the phases, and re-extract the aqueous phase with EtOAc. Dry the combined organic phases over MgSO4 and remove the solvent under vacuum. Purify the crude product by column chromatography (CH2Cl2/MeOH/NH4OH 9:2:0.25) to obtain 8.9 g of a colorless oil LC/MS, (LiChrospher 5μ, RP-18, 250 mm CH3CN/Water(0.05% TFA)-gradient 2%→98% (20 min), Flow: 0.75 mL/min), tR=7.79 min, m/z=321.3.