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【结 构 式】

【分子编号】46532

【品名】(4S)-4-(dibenzylamino)-4-phenyl-1-butanol

【CA登记号】

【 分 子 式 】C24H27NO

【 分 子 量 】345.48452

【元素组成】C 83.44% H 7.88% N 4.05% O 4.63%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(VII)

A new total synthesis of sertraline has been described: The reduction of N,N-dibenzyl-D-phenylglycine methyl ester (I) with LiAlH4 in THF gives alcohol (II), which is oxidized to aldehyde (III) with oxalyl chloride in dichloromethane. The condensation of (III) with the phosphorane (IV) in benzene yields the unsaturated ester (V), which is reduced with Mg in methanol affording the saturated methyl ester (VI). Reduction of (VI) with LiAlH4 in THF provides the corresponding butanol derivative (VII), which is oxidized to the aldehyde (VIII) with pyridinium dichromate (PDC) in dichloromethane. The Grignard reaction of (VIII) with 3,4-dichlorophenylmagnesium bromide (IX) in THF affords the secondary alcohol (X), which is cyclized by means of AlCl3 in dichloromethane yielding a mixture of the desired cis-isomer (XI) along with some trans-isomer separated by column chromatography. Debenzylation of (XI) by H2 over Pd(OH)2 in methanol, followed by protection with Boc2O yields the carbamate (XII), which is methylated with methyl iodide and NaH in THF to afford the protected intermediate (XIII). Finally, compound (XIII) is deprotected with TFA in dichloromethane.

1 Chandrasekhar, S.; Reddy, M.V.; An expedient total synthesis of cis-(+)-sertraline from D-phenylglycine. Tetrahedron 2000, 56, 8, 1111.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 46527 methyl (2R)-2-(dibenzylamino)-2-phenylethanoate C23H23NO2 详情 详情
(II) 46528 (2R)-2-(dibenzylamino)-2-phenyl-1-ethanol C22H23NO 详情 详情
(III) 46529 (2R)-2-(dibenzylamino)-2-phenylethanal C22H21NO 详情 详情
(IV) 14182 ethyl 2-(triphenyl-lambda(5)-phosphanylidene)acetate; (Carbethoxymethylene)triphenylphosphorane 1099-45-2 C22H21O2P 详情 详情
(V) 46530 ethyl (E,4S)-4-(dibenzylamino)-4-phenyl-2-butenoate C26H27NO2 详情 详情
(VI) 46531 methyl (4S)-4-(dibenzylamino)-4-phenylbutanoate C25H27NO2 详情 详情
(VII) 46532 (4S)-4-(dibenzylamino)-4-phenyl-1-butanol C24H27NO 详情 详情
(VIII) 46533 (4S)-4-(dibenzylamino)-4-phenylbutanal C24H25NO 详情 详情
(IX) 10069 Bromo(3,4-dichlorophenyl)magnesium 79175-35-2 C6H3BrCl2Mg 详情 详情
(X) 46534 (4S)-4-(dibenzylamino)-1-(3,4-dichlorophenyl)-4-phenyl-1-butanol C30H29Cl2NO 详情 详情
(XI) 46535 N,N-dibenzyl-N-[(1S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenyl]amine; (1S,4S)-N,N-dibenzyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine C30H27Cl2N 详情 详情
(XII) 46536 tert-butyl (1S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenylcarbamate C21H23Cl2NO2 详情 详情
(XIII) 46537 tert-butyl (1S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenyl(methyl)carbamate C22H25Cl2NO2 详情 详情
Extended Information