(4S)-4-methylhexyl methanesulfonate -Drug Synthesis Database

【结构式】

【分子编号】41602

【品名】(4S)-4-methylhexyl methanesulfonate

【CA登记号】

【分子式】C₈H₁₈O₃S

【分子量】194.29512

【元素组成】C 49.45% H 9.34% O 24.7% S 16.5%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(IX)

The alkylation of 4-(tert-butoxycarbonylamino)piperidine (VIII) with (S)-4- methylhexyl methanesulfonate (IX) provided the tertiary amine (X). Cleavage of the Boc protecting group of (X) gave aminopiperidine (XI), which was finally coupled with the chiral hydroxyacid (IV) by means of carbonyl diimidazole.

参考文献中间体

合成目标

【1】 Tsuchiya, Y.; Nomoto, T.; Ohsawa, H.; Kawakami, K.; Ohwaki, K.; Nishikibe, M. (Banyu Pharmaceutical Co., Ltd.); 1,4-Disubstd. piperidine derivs.. EP 0823423; US 5750540; WO 9633973 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VIII)	41601	tert-butyl 4-piperidinylcarbamate; 4-tert-Boc-aminopiperidine	73874-95-0	C₁₀H₂₀N₂O₂	详情	详情
(IX)	41602	(4S)-4-methylhexyl methanesulfonate		C₈H₁₈O₃S	详情	详情
(X)	41603	tert-butyl 1-[(4S)-4-methylhexyl]-4-piperidinylcarbamate		C₁₇H₃₄N₂O₂	详情	详情
(XI)	41604	1-[(4S)-4-methylhexyl]-4-piperidinylamine; 1-[(4S)-4-methylhexyl]-4-piperidinamine		C₁₂H₂₆N₂	详情	详情
(XII)	31466	(2R)-2-cyclopentyl-2-hydroxy-2-phenylethanoic acid		C₁₃H₁₆O₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(IX)

In a related procedure, hydroxyacid (IV) was coupled with 1-Boc-4-aminopiperidine (XII) employing EDC and HOBt to give amide (XIII). Acid cleavage of the Boc group of (XIII) yielded amine (XIV), that was finally alkylated with mesylate (IX).

参考文献中间体

合成目标

【1】 Yamakawa, T.; et al.; Synthesis and structure-activity-relationships of 4-acetamidopiperidines as M3 selective antagonists. 15th European Federation for Medicinal Chemistry International Symposium on Medicinal Chemistry (Sept 6 1998, Edinburgh) 1998, Abst P.294.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IV)	31466	(2R)-2-cyclopentyl-2-hydroxy-2-phenylethanoic acid		C₁₃H₁₆O₃	详情	详情
(IX)	41602	(4S)-4-methylhexyl methanesulfonate		C₈H₁₈O₃S	详情	详情
(XII)	28414	4-Amino-1-N-Boc-piperidine; tert-butyl 4-amino-1-piperidinecarboxylate; N-Boc-4-aminopiperidine	87120-72-7	C₁₀H₂₀N₂O₂	详情	详情
(XIII)	41605	tert-butyl 4-[[(2R)-2-cyclopentyl-2-hydroxy-2-phenylethanoyl]amino]-1-piperidinecarboxylate		C₂₃H₃₄N₂O₄	详情	详情
(XIV)	41606	(2R)-2-cyclopentyl-2-hydroxy-2-phenyl-N-(4-piperidinyl)ethanamide		C₁₈H₂₆N₂O₂	详情	详情

Extended Information