[(3R)-1-[(1R)-1-phenylethyl]pyrrolidinyl]methanol -Drug Synthesis Database

【结构式】

【分子编号】34461

【品名】[(3R)-1-[(1R)-1-phenylethyl]pyrrolidinyl]methanol

【CA登记号】

【分子式】C₁₃H₁₉NO

【分子量】205.3

【元素组成】C 76.06% H 9.33% N 6.82% O 7.79%

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：(I)

Hydrogenation of the enantiomerically pure 1-(alpha-methylbenzyl)-3-(hydroxymethyl)pyrrolidine (I) in the presence of Pearlman's catalyst and di-tert-butyl dicarbonate produced the N-Boc pyrrolidine (II). Reaction of (II) with methanesulfonyl chloride, followed by condensation of the resulting mesylate (III) with (S)-alpha-methylbenzylamine (IV) in toluene at 150 C in a sealed tube afforded the aminomethyl pyrrolidine derivative (V). Then, acidic cleavage of the Boc protecting group yielded pyrrolidine (VI).

参考文献中间体

合成目标

【1】 Sternfeld, F.; Guiblin, A.R.; Jelley, R.A.; et al.; Synthesis and serotonergic activity of 3-[2-(pyrrolidin-1-yl)ethyl]indoles: Potent agonists for the h5-HT1D receptor with high selectivity over the h5-HT1B receptor. J Med Chem 1999, 42, 4, 677.
【2】 Ogawa, T.; Terai, T.; Haruna, K.; Watanabe, A.; Tominaga, T.; Taguchi, H. (Senju Pharmaceuticals Co., Ltd.; Toyobo Co., Ltd.); Pharmaceutical compsn. for topical administration to the eye for treating allergic conjunctivitis. CA 2165999; EP 0719553; JP 1996231393 .

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)	34461	[(3R)-1-[(1R)-1-phenylethyl]pyrrolidinyl]methanol		C₁₃H₁₉NO	详情	详情
(II)	34462	tert-butyl (3R)-3-(hydroxymethyl)-1-pyrrolidinecarboxylate		C₁₀H₁₉NO₃	详情	详情
(III)	34463	1-Boc-3-methanesulfonyloxymethylpyrrolidine; 1-Boc-3-methanesulfonyloxymethylpyrrolidine	141699-56-1	C₁₁H₂₁NO₅S	详情	详情
(IV)	20042	(1S)-1-phenyl-1-ethanamine; (1S)-1-phenylethylamine		C₈H₁₁N	详情	详情
(V)	34464	tert-butyl (3S)-3-([[(1S)-1-phenylethyl]amino]methyl)-1-pyrrolidinecarboxylate		C₁₈H₂₈N₂O₂	详情	详情
(VI)	34465	N-[(1S)-1-phenylethyl]-N-[(3R)pyrrolidinylmethyl]amine; (1S)-1-phenyl-N-[(3R)pyrrolidinylmethyl]-1-ethanamine		C₁₃H₂₀N₂	详情	详情

Extended Information