N-methyl-N-[(1S)-3-(1-naphthyloxy)-1-phenylpropyl]amine; (1S)-N-methyl-3-(1-naphthyloxy)-1-phenyl-1-propanamine -Drug Synthesis Database

【结构式】

【分子编号】59232

【品名】N-methyl-N-[(1S)-3-(1-naphthyloxy)-1-phenylpropyl]amine; (1S)-N-methyl-3-(1-naphthyloxy)-1-phenyl-1-propanamine

【CA登记号】

【分子式】C₂₀H₂₁NO

【分子量】291.39288

【元素组成】C 82.44% H 7.26% N 4.81% O 5.49%

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：(XXI)

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.

参考文献中间体

合成目标

【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

Extended Information