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【结 构 式】 
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【分子编号】59234 【品名】(3R)-3-hydroxy-3-phenylpropyl 4-methylbenzenesulfonate 【CA登记号】 |
【 分 子 式 】C16H18O4S 【 分 子 量 】306.38252 【元素组成】C 62.72% H 5.92% O 20.89% S 10.47% |
合成路线1
该中间体在本合成路线中的序号：(I)In an improved method, the acetamido isophthalamide (I) is treated with boric acid and KOH to form the cyclic diborate tripotassium salt (II). Subsequent alkylation of (II) with 2-chloroethanol (III) yields regioselectively the N-alkylated acetamide (IV). The borate groups of (IV) are finally removed upon quenching with diluted HCl.
| 【1】 Bjoersvik, H.-R.; et al.; A selective process for N-alkylation in competition with O-alkylation: Boric acid, borax, and metaborate as a cheap and effective protecting group applicable for industrial-scale synthetic processes. Org Process Res Dev 2001, 5, 5, 472. |
| 【2】 Priebe, H. (Amersham plc); An N-alkylation. GB 2331098 . |
合成路线2
该中间体在本合成路线中的序号：(XVII)The synthesis of the [11C]-labeled compound was also reported. Selective tosylation of the primary hydroxyl of (R)-1-phenyl-1,3-propanediol (XVI) provided (XVII). From this, naphthyl ether (XIX) was prepared by Williamson's synthesis with the sodium alkoxide of 1-naphthol (XVIII). The remaining hydroxyl group of (XIX) was then converted to mesylate (XX) upon treatment with methanesulfonyl chloride and DMAP. Subsequent displacement with methylamine in a sealed vessel afforded the secondary amine (XXI). This was finally alkylated with 11CH3I to yield the target 11C-labeled compound.
| 【1】 Livni, E.; et al.; Synthesis of [11C]dapoxetine.HCl, a serotonin re-uptake inhibitor: biodistribution in rat and preliminary PET imaging in the monkey. Nucl Med Biol 1994, 21, 4, 669. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XVI) | 59233 | (R)-(+)-1-phenyl-1,3-propanediol; (R)-1-Phenyl-1,3-propanediol | 103548-16-9 | C9H12O2 | 详情 | 详情 |
| (XVII) | 59234 | (3R)-3-hydroxy-3-phenylpropyl 4-methylbenzenesulfonate | C16H18O4S | 详情 | 详情 | |
| (XVIII) | 22935 | alpha-naphthol; 1-naphthol | 90-15-3 | C10H8O | 详情 | 详情 |
| (XIX) | 59230 | (1R)-3-(1-naphthyloxy)-1-phenyl-1-propanol | C19H18O2 | 详情 | 详情 | |
| (XX) | 59231 | (1R)-3-(1-naphthyloxy)-1-phenylpropyl methanesulfonate | C20H20O4S | 详情 | 详情 | |
| (XXI) | 59232 | N-methyl-N-[(1S)-3-(1-naphthyloxy)-1-phenylpropyl]amine; (1S)-N-methyl-3-(1-naphthyloxy)-1-phenyl-1-propanamine | C20H21NO | 详情 | 详情 |