【结 构 式】 |
【分子编号】31453 【品名】(3S)-1-[(2S)-2-(methylamino)-2-phenylethyl]-3-pyrrolidinol 【CA登记号】 |
【 分 子 式 】C13H20N2O 【 分 子 量 】220.31468 【元素组成】C 70.87% H 9.15% N 12.72% O 7.26% |
合成路线1
该中间体在本合成路线中的序号:(V)The condensation of (S)-phenylglycine (I) with ethyl chloroformate gave carbamate (II). After activation of (II) as the mixed anhydride with ethyl chloroformate in the presence of N-methylmorpholine, coupling with (S)-3-hydroxypyrrolidine (III) provided amide (IV). Reduction of both amide and carbamate groups of (IV) employing LiAlH4 in refluxing THF yielded diamine (V). This was finally condensed with diphenylacetyl chloride (VI) to furnish the title amide The condensation of (S)-phenylglycine (I) with ethyl chloroformate gave carbamate (II). After activation of (II) as the mixed anhydride with ethyl chloroformate in the presence of N-methylmorpholine, coupling with (S)-3-hydroxypyrrolidine (III) provided amide (IV). Reduction of both amide and carbamate groups of (IV) employing LiAlH4 in refluxing THF yielded diamine (V). This was finally condensed with diphenylacetyl chloride (VI) to furnish the title amide.
【1】 Ackermann, K.-A.; Budak, J.; Bathe, A.; Gottschlich, R.; Helfert, B.; Stein, I. (Merck Patent GmbH); Method for producing enantiomer-free N-methyl-N-[(1S)-1-phenyl-2-((3S)-3-hydroxypyrrolidine-1-yl)ethyl]-2,2-diphenyl acetamide. DE 19827633; WO 9954298 . |
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) | 10716 | (2S)-2-Amino-2-phenylethanoic acid; L-(+)-alpha-Phenylglycine | 2935-35-5 | C8H9NO2 | 详情 | 详情 |
(II) | 12171 | (2S)-2-[(Ethoxycarbonyl)amino]-2-phenylethanoic acid | C11H13NO4 | 详情 | 详情 | |
(III) | 14490 | (3R)tetrahydro-1H-pyrrol-3-ol; R-3-hydroxypyrrolidine | 2799-21-5 | C4H9NO | 详情 | 详情 |
(IV) | 31452 | ethyl (1S)-2-[(3S)-3-hydroxypyrrolidinyl]-2-oxo-1-phenylethylcarbamate | C15H20N2O4 | 详情 | 详情 | |
(V) | 31453 | (3S)-1-[(2S)-2-(methylamino)-2-phenylethyl]-3-pyrrolidinol | C13H20N2O | 详情 | 详情 | |
(VI) | 23800 | Diphenylacetyl chloride; 2,2-diphenylacetyl chloride | 1871-76-7 | C14H11ClO | 详情 | 详情 |