Tetrahydrofuran → HCID 58869125, 화합물

반응식

C[O:2][C:3](=O)[CH2:4][NH:5][CH2:6][C@H:7]1[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][C:11]([S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)(=[O:19])=[O:18])=[CH:12][CH:13]=2)[O:8]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:33]1COCC1>>[C:20]1([S:17]([C:11]2[CH:10]=[C:9]3[C:14]([CH2:15][CH2:16][C@H:7]([CH2:6][N:5]([CH3:33])[CH2:4][CH2:3][OH:2])[O:8]3)=[CH:13][CH:12]=2)(=[O:18])=[O:19])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

반응물 3

HCID 8028Tetrahydrofuran

HCID 21226445Aluminium lithium hydride

HCID 58869158HCID 58869158, 화합물

생성물 1

HCID 58869125HCID 58869125, 화합물

실험 절차

(R)-[(7-benzenesulfonyl-chroman-2-ylmethyl)-amino]-acetic acid methyl ester (40 mg, 1 mmol) was dissolved in 2 mL dry THF under Ar atmosphere. LAH (0.25 mL of 1M solution in THF) was added dropwise, and the reaction mixture was stirred for one hour. The reaction was quenched by addition of aqueous sodium sulfate solution. The mixture was extracted with methylene chloride and the combined organic layers were washed with water and brine, dried (Na2SO4), filtered and contrated under reduced pressure. The residue was recrystallized from diethyl ether and 1 M HCl in EtOH to give 32.2 mg of (R)-2-[(7-Benzenesulfonyl-chroman-2-ylmethyl)-methyl-amino]-ethanol as a hydrochloride, MS (M+H)=362.