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【结 构 式】

【分子编号】65130

【品名】(3R,4S)-1-benzyl-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-(3-fluorophenyl)pyrrolidine; [(3R,4S)-1-benzyl-4-(3-fluorophenyl)pyrrolidinyl]methyl tert-butyl(dimethyl)silyl ether

【CA登记号】

【 分 子 式 】C24H34FNOSi

【 分 子 量 】399.6240032

【元素组成】C 72.13% H 8.58% F 4.75% N 3.5% O 4% Si 7.03%

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:(VIII)

m-Fluorocinnamic acid (I) is coupled to (S)-4-benzyloxazolidin-2-one (II), via the corresponding mixed anhydride with pivaloyl chloride, to furnish the N-cinnamoyl oxazolidinone (III). Cycloaddition of (III) with N-methoxymethyl-N-trimethylsilylmethyl benzylamine (IV) in the presence of trifluoroacetic acid produces a mixture of the diastereoisomeric pyrrolidines (V) and (VI), separable by column chromatography. The desired isomer (V) is then reduced by means of LiAlH4 to the primary alcohol (VII), which is further protected by silylation with t-butyldimethylsilyl chloride. The resultant silyl ether (VIII) is then subjected to benzyl group cleavage under transfer hydrogenation conditions, producing pyrrolidine (IX) (1).

1 Mills, S.G.; Kim, D.; Hale, J.; MacCoss, M.; Berk, S.; Chapman, K.; Lynch, C.; Caldwell, C.; Willoughby, C.; Rosauer, K. (Merck & Co., Inc.); Pyrrolidine modulators of chemokine receptor activity. US 6265434; WO 0059503 .
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) 63980 m-Fluorocinnamic acid; (E)-3-(3-fluorophenyl)-2-propenoic acid C9H7FO2 详情 详情
(II) 25351 (4R)-4-benzyl-1,3-oxazolidin-2-one; (R)-(+)-4-benzyl-2-oxazolidinone 102029-44-7 C10H11NO2 详情 详情
(III) 63983 (4S)-4-benzyl-3-[(E)-3-(3-fluorophenyl)-2-propenoyl]-1,3-oxazolidin-2-one C19H16FNO3 详情 详情
(IV) 25556 N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine; N-benzyl-N-(methoxymethyl)(trimethylsilyl)methanamine 1871-96-1 C13H23NOSi 详情 详情
(V) 63985 (4S)-4-benzyl-3-{[(3R,4S)-1-benzyl-4-(3-fluorophenyl)pyrrolidinyl]carbonyl}-1,3-oxazolidin-2-one C28H27FN2O3 详情 详情
(VI) 63984 (4S)-4-benzyl-3-{[(3S,4R)-1-benzyl-4-(3-fluorophenyl)pyrrolidinyl]carbonyl}-1,3-oxazolidin-2-one C28H27FN2O3 详情 详情
(VII) 63986 [(3R,4S)-1-benzyl-4-(3-fluorophenyl)pyrrolidinyl]methanol C18H20FNO 详情 详情
(VIII) 65130 (3R,4S)-1-benzyl-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-(3-fluorophenyl)pyrrolidine; [(3R,4S)-1-benzyl-4-(3-fluorophenyl)pyrrolidinyl]methyl tert-butyl(dimethyl)silyl ether C24H34FNOSi 详情 详情
(IX) 63988 (3R,4S)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-(3-fluorophenyl)pyrrolidine; tert-butyl(dimethyl)silyl [(3R,4S)-4-(3-fluorophenyl)pyrrolidinyl]methyl ether C17H28FNOSi 详情 详情
Extended Information