2-[(2R)-4-benzoyl-2-(3,4-difluorophenyl)morpholinyl]ethyl methanesulfonate -Drug Synthesis Database

【结构式】

【分子编号】54992

【品名】2-[(2R)-4-benzoyl-2-(3,4-difluorophenyl)morpholinyl]ethyl methanesulfonate

【CA登记号】

【分子式】C₂₀H₂₁F₂NO₅S

【分子量】425.4532864

【元素组成】C 56.46% H 4.98% F 8.93% N 3.29% O 18.8% S 7.54%

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：(XIV)

Benzamide (XII) was prepared by acylation of morpholine (X) with benzoyl chloride (XI). The benzoate ester of (XII) was subsequently hydrolyzed under basic conditions to the alcohol (XIII), which was further converted to the mesylate ester (XIV) by means of methanesulfonyl chloride and triethylamine.

参考文献中间体

合成目标

【1】 Emonds-Alt, X.; Grossriether, I.; Gueule, P.; Proietto, V.; Van Broeck, D. (Sanofi-Synthélabo); Substd. heterocyclic cpds., preparation method therefor and pharmaceutical compsns. containing same. EP 1156049; FR 2729952; FR 2729953; FR 2729954; JP 1999507324; JP 2001131171; US 5641777; WO 9623787 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(X)	54989	2-[(2R)-2-(3,4-difluorophenyl)morpholinyl]ethyl benzoate		C₁₉H₁₉F₂NO₃	详情	详情
(XI)	10463	Benzoyl chloride	98-88-4	C₇H₅ClO	详情	详情
(XII)	54990	2-[(2R)-4-benzoyl-2-(3,4-difluorophenyl)morpholinyl]ethyl benzoate		C₂₆H₂₃F₂NO₄	详情	详情
(XIII)	54991	[(2R)-2-(3,4-difluorophenyl)-2-(2-hydroxyethyl)morpholinyl](phenyl)methanone		C₁₉H₁₉F₂NO₃	详情	详情
(XIV)	54992	2-[(2R)-4-benzoyl-2-(3,4-difluorophenyl)morpholinyl]ethyl methanesulfonate		C₂₀H₂₁F₂NO₅S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XIV)

Acetamide (XVI) was obtained by the Ritter reaction of 1-benzyl-4-phenyl-piperidin-4-ol (XV) with acetonitrile. Acidic hydrolysis of amide (XVI) provided the aminopiperidine (XVII), which was converted into urea (XVIII) upon treatment with N,N-dimethylcarbamoyl chloride. Hydrogenolytic cleavage of the N-benzyl group of (XVIII) gave piperidine (XIX), which was finally alkylated with the mesylate (XIV) to furnish the title compound.

参考文献中间体

合成目标

【1】 Emonds-Alt, X.; Grossriether, I.; Gueule, P.; Proietto, V.; Van Broeck, D. (Sanofi-Synthélabo); Substd. heterocyclic cpds., preparation method therefor and pharmaceutical compsns. containing same. EP 1156049; FR 2729952; FR 2729953; FR 2729954; JP 1999507324; JP 2001131171; US 5641777; WO 9623787 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XIV)	54992	2-[(2R)-4-benzoyl-2-(3,4-difluorophenyl)morpholinyl]ethyl methanesulfonate	C₂₀H₂₁F₂NO₅S	详情	详情
(XV)	29470	1-benzyl-4-phenyl-4-piperidinol	C₁₈H₂₁NO	详情	详情
(XVI)	54993	N-(1-benzyl-4-phenyl-4-piperidinyl)acetamide	C₂₀H₂₄N₂O	详情	详情
(XVII)	54994	1-benzyl-4-phenyl-4-piperidinylamine; 1-benzyl-4-phenyl-4-piperidinamine	C₁₈H₂₂N₂	详情	详情
(XVIII)	54995	N'-(1-benzyl-4-phenyl-4-piperidinyl)-N,N-dimethylurea	C₂₁H₂₇N₃O	详情	详情
(XIX)	54996	N,N-dimethyl-N'-(4-phenyl-4-piperidinyl)urea	C₁₄H₂₁N₃O	详情	详情

Extended Information