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【结 构 式】 
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【分子编号】53064 【品名】benzyl 4-(hydroxymethyl)-4,8,8-trimethyl-6,10-dioxa-2-azaspiro[4.5]decane-2-carboxylate 【CA登记号】n/a |
【 分 子 式 】C19H27NO5 【 分 子 量 】349.42712 【元素组成】C 65.31% H 7.79% N 4.01% O 22.89% |
合成路线1
该中间体在本合成路线中的序号：(XIII)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).
| 【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 |