(1S,2R)-2-[(1S)-1-hydroxypropyl]-1-phenyl-N,N-dipropylcyclopropanecarboxamide -Drug Synthesis Database

【结构式】

【分子编号】61473

【品名】(1S,2R)-2-[(1S)-1-hydroxypropyl]-1-phenyl-N,N-dipropylcyclopropanecarboxamide

【CA登记号】

【分子式】C₁₉H₂₉NO₂

【分子量】303.4448

【元素组成】C 75.21% H 9.63% N 4.62% O 10.55%

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：(IV)

The title compound is synthesized from the optically active lactone (I). Aluminum chloride-catalyzed aminolysis of (I) with dipropylamine affords the hydroxy amide (II). Subsequent Swern oxidation of the alcohol function of (II) leads to aldehyde (III). Addition of ethylmagnesium bromide to aldehyde (III) then stereoselectively provides the (S)-alcohol adduct (IV). Introduction of an azido group in (IV) by using a Mitsunobu-type reaction leads to configuration-retained azide (V). This is finally reduced to the desired amine by catalytic hydrogenation in the presence of Pd/C

参考文献中间体

合成目标

【1】 Kazuta, Y.; et al.; Synthesis of (1S,2R)-1-phenyl-2-[(S)-1-aminopropyl]-N, N-diethylcyclopropanecarboxamide (PPDC) derivatives modified at the carbamoyl moiety as a new class of NMDA receptor antagonists. Bioorg. Med. Chem. 2002, 10, 6, 1777.

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)	61470	(1S,5R)-1-phenyl-3-oxabicyclo[3.1.0]hexan-2-one	63106-93-4	C₁₁H₁₀O₂	详情	详情
(II)	61471	(1S,2R)-2-(hydroxymethyl)-1-phenyl-N,N-dipropylcyclopropanecarboxamide		C₁₇H₂₅NO₂	详情	详情
(III)	61472	(1S,2R)-2-formyl-1-phenyl-N,N-dipropylcyclopropanecarboxamide		C₁₇H₂₃NO₂	详情	详情
(IV)	61473	(1S,2R)-2-[(1S)-1-hydroxypropyl]-1-phenyl-N,N-dipropylcyclopropanecarboxamide		C₁₉H₂₉NO₂	详情	详情
(V)	61474	(1S,2R)-2-[(1S)-1-azidopropyl]-1-phenyl-N,N-dipropylcyclopropanecarboxamide		C₁₉H₂₈N₄O	详情	详情

Extended Information