1-(tert-butyl) 2-methyl (2S)-1,2-pyrrolidinedicarboxylate -Drug Synthesis Database

【结构式】

【分子编号】50435

【品名】1-(tert-butyl) 2-methyl (2S)-1,2-pyrrolidinedicarboxylate

【CA登记号】

【分子式】C₁₁H₁₉NO₄

【分子量】229.2762

【元素组成】C 57.63% H 8.35% N 6.11% O 27.91%

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：(XI)

Fischer esterification of L-proline (IX) with MeOH and HCl gave (X). Treatment of (X) with di-tert-butyl dicarbonate provided N-Boc-proline methyl ester (XI). The ester function of (XI) was then reduced to aldehyde (XII) by employing DIBAL in toluene at -78 C. Wittig condensation between aldehyde (XII) and phosphonium bromide (VIII) in the presence of DBU yielded the (indolylvinyl)pyrrolidine (XIII), which was further hydrogenated to (XIV) in the presence of Pd/C. The N-Boc group of (XIV) was then cleaved by treatment with trifluoroacetic acid to furnish (XV).

参考文献中间体

合成目标

【1】 Koo, B.A.; Min, J.K.; Hong, W.S.; Ryu, E.J.; Nam, W.H.; Kim, J.M. (C & C Research Laboratories); Aromatic amidine derivs. useful as selective thrombin inhibitors. EP 0918768; JP 2000504030; US 6201006; WO 9745424 .

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)	50434	[(6-cyano-1-ethyl-1H-indol-2-yl)methyl](triphenyl)phosphonium bromide		C₃₀H₂₆BrN₂P	详情	详情
(IX)	16731	L-proline	147-85-3	C₅H₉NO₂	详情	详情
(X)	29552	methyl (2S)-2-pyrrolidinecarboxylate	2133-40-6	C₆H₁₁NO₂	详情	详情
(XI)	50435	1-(tert-butyl) 2-methyl (2S)-1,2-pyrrolidinedicarboxylate		C₁₁H₁₉NO₄	详情	详情
(XII)	16724	tert-Butyl (2S)-2-formyltetrahydro-1H-pyrrole-1-carboxylate; tert-Butoxycarbonyl-L-prolinal	69610-41-9	C₁₀H₁₇NO₃	详情	详情
(XIII)	50436	tert-butyl (2S)-2-[(E)-2-(6-cyano-1-ethyl-1H-indol-2-yl)ethenyl]-1-pyrrolidinecarboxylate		C₂₂H₂₇N₃O₂	详情	详情
(XIV)	50437	tert-butyl (2S)-2-[2-(6-cyano-1-ethyl-1H-indol-2-yl)ethyl]-1-pyrrolidinecarboxylate		C₂₂H₂₉N₃O₂	详情	详情
(XV)	50438	1-ethyl-2-[2-[(2S)pyrrolidinyl]ethyl]-1H-indole-6-carbonitrile		C₁₇H₂₁N₃	详情	详情

Extended Information