benzyl 4-(azidomethyl)-4,8,8-trimethyl-6,10-dioxa-2-azaspiro[4.5]decane-2-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】53066

【品名】benzyl 4-(azidomethyl)-4,8,8-trimethyl-6,10-dioxa-2-azaspiro[4.5]decane-2-carboxylate

【CA登记号】n/a

【分子式】C₁₉H₂₆N₄O₄

【分子量】374.44

【元素组成】C 60.95% H 7% N 14.96% O 17.09%

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：(XV)

In a similar procedure, ester (IV) was reduced to the corresponding alcohol (XIII) using LiAlH4. After conversion of (XIII) to the corresponding mesylate (XIV), displacement by NaN3 provided azide (XV). Reduction of (XV) to the primary amine (XVI) was effected by treatment with PPh3 in moist acetonitrile. Resolution of the racemic amine (XVI) was achieved by acylation with N-tosyl-L-proline (IX) followed by chromatographic separation. The desired isomer (XVII) was hydrolyzed with KOH in isopropanol, and the resultant amine was further protected as the N-Boc derivative (XVIII). Catalytic hydrogenolysis of (XVIII) then provided the target pyrrolidine (XII).

参考文献中间体

合成目标

【1】 Lee, C.-W.; et al.; Synthesis antibacterial activities of DW286, a new fluoronaphthyridone antibiotic as an enantiomer. 41st Intersci Conf Antimicrob Agents Chemother (Dec 16 2001, Chicago) 2001, Abst F-553.

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)	53055	2-benzyl 4-ethyl 4,8,8-trimethyl-6,10-dioxa-2-azaspiro[4.5]decane-2,4-dicarboxylate	n/a	C₂₁H₂₉NO₆	详情	详情
(IX)	50360	2-amino-6-(4-[(E)-3-[4-(3,5-difluorophenyl)-1-piperazinyl]-1-propenyl]-5-methyl-1H-pyrazol-1-yl)-4-pyrimidinol		C₂₁H₂₃F₂N₇O	详情	详情
(XII)	53063	tert-butyl [(4S)-4,8,8-trimethyl-6,10-dioxa-2-azaspiro[4.5]dec-4-yl]methylcarbamate	n/a	C₁₆H₃₀N₂O₄	详情	详情
(XIII)	53064	benzyl 4-(hydroxymethyl)-4,8,8-trimethyl-6,10-dioxa-2-azaspiro[4.5]decane-2-carboxylate	n/a	C₁₉H₂₇NO₅	详情	详情
(XIV)	53065	benzyl 4,8,8-trimethyl-4-{[(methylsulfonyl)oxy]methyl}-6,10-dioxa-2-azaspiro[4.5]decane-2-carboxylate	n/a	C₂₀H₂₉NO₇S	详情	详情
(XV)	53066	benzyl 4-(azidomethyl)-4,8,8-trimethyl-6,10-dioxa-2-azaspiro[4.5]decane-2-carboxylate	n/a	C₁₉H₂₆N₄O₄	详情	详情
(XVI)	53067	benzyl 4-(aminomethyl)-4,8,8-trimethyl-6,10-dioxa-2-azaspiro[4.5]decane-2-carboxylate	n/a	C₁₉H₂₈N₂O₄	详情	详情
(XVII)	53068	benzyl (4R)-4,8,8-trimethyl-4-{[({(2S)-1-[(4-methylphenyl)sulfonyl]pyrrolidinyl}carbonyl)amino]methyl}-6,10-dioxa-2-azaspiro[4.5]decane-2-carboxylate	n/a	C₃₁H₄₁N₃O₇S	详情	详情
(XVIII)	53069	benzyl (4R)-4-{[(tert-butoxycarbonyl)amino]methyl}-4,8,8-trimethyl-6,10-dioxa-2-azaspiro[4.5]decane-2-carboxylate	n/a	C₂₄H₃₆N₂O₆	详情	详情

Extended Information