tert-butyl 4-(allylamino)-1-piperidinecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】43903

【品名】tert-butyl 4-(allylamino)-1-piperidinecarboxylate

【CA登记号】

【分子式】C₁₃H₂₄N₂O₂

【分子量】240.34584

【元素组成】C 64.97% H 10.06% N 11.66% O 13.31%

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：(III)

Reductive amination of N-Boc-4-piperidone (I) with allylamine (II) in the presence of sodium triacetoxyborohydride afforded aminopiperidine (III), which was acylated with 4-nitrobenzyl chloroformate (IV) to yield carbamate (V). Removal of the Boc group of (V) by means of a methanolic solution of HCl, prepared from acetyl chloride and MeOH, provided piperidine (VI).

参考文献中间体

合成目标

【1】 Finke, P.E.; Mills, S.G.; Caldwell, C.G.; MacCoss, M.; Wang, L.; Kothandaraman, S.; Kim, D.; Oates, B. (Merck & Co., Inc.); Cyclic amine modulators of chemokine receptor activity. EP 1052992; US 6140349; WO 9938514 .

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)	18620	tert-butyl 4-oxo-1-piperidinecarboxylate;BOC-Piperidone;N-(tert-Butoxycarbonyl)-4-piperidone; N-Boc-4-piperidone	79099-07-3	C₁₀H₁₇NO₃	详情	详情
(II)	13672	Allylamine; 2-Propen-1-amine	107-11-9	C₃H₇N	详情	详情
(III)	43903	tert-butyl 4-(allylamino)-1-piperidinecarboxylate		C₁₃H₂₄N₂O₂	详情	详情
(IV)	33055	1-[[(chlorocarbonyl)oxy]methyl]-4-nitrobenzene	4457-32-3	C₈H₆ClNO₄	详情	详情
(V)	43904	tert-butyl 4-(allyl[[(4-nitrobenzyl)oxy]carbonyl]amino)-1-piperidinecarboxylate		C₂₁H₂₉N₃O₆	详情	详情
(VI)	43905	4-nitrobenzyl allyl(4-piperidinyl)carbamate		C₁₆H₂₁N₃O₄	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

Reductive amination of N-Boc-4-piperidone (I) with allyl amine (II) in the presence of sodium triacetoxyborohydride gave aminopiperidine (III), which was condensed with 4-nitrobenzyl chloroformate (IV) to afford carbamate (V). The Boc group of (V) was then cleaved by treatment with methanolic HCl to produce intermediate piperidine (VI). Alternatively, the condensation of 1-Boc-piperidine-4-amine (VII) with chloroformate (IV) gives carbamate (VIII), which is allylated with allyl chloride (IX) and NaH in THF, yielding the already reported carbamate (V).

参考文献中间体

合成目标

【1】 Chen, P.; Dorn, C.P. Jr.; Caldwell, C.G.; et al.; Synthesis and evaluation of CCR5 antagonists having potent in vitro antiviral activity. 220th ACS Natl Meet (Aug 20 2000, Washington DC) 2000, Abst MEDI 85.
【2】 Finke, P.E.; Mills, S.G.; Caldwell, C.G.; MacCoss, M.; Wang, L.; Kothandaraman, S.; Kim, D.; Oates, B. (Merck & Co., Inc.); Cyclic amine modulators of chemokine receptor activity. EP 1052992; US 6140349; WO 9938514 .

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)	18620	tert-butyl 4-oxo-1-piperidinecarboxylate;BOC-Piperidone;N-(tert-Butoxycarbonyl)-4-piperidone; N-Boc-4-piperidone	79099-07-3	C₁₀H₁₇NO₃	详情	详情
(II)	13672	Allylamine; 2-Propen-1-amine	107-11-9	C₃H₇N	详情	详情
(III)	43903	tert-butyl 4-(allylamino)-1-piperidinecarboxylate		C₁₃H₂₄N₂O₂	详情	详情
(IV)	33055	1-[[(chlorocarbonyl)oxy]methyl]-4-nitrobenzene	4457-32-3	C₈H₆ClNO₄	详情	详情
(V)	43904	tert-butyl 4-(allyl[[(4-nitrobenzyl)oxy]carbonyl]amino)-1-piperidinecarboxylate		C₂₁H₂₉N₃O₆	详情	详情
(VI)	43905	4-nitrobenzyl allyl(4-piperidinyl)carbamate		C₁₆H₂₁N₃O₄	详情	详情
(VII)	28414	4-Amino-1-N-Boc-piperidine; tert-butyl 4-amino-1-piperidinecarboxylate; N-Boc-4-aminopiperidine	87120-72-7	C₁₀H₂₀N₂O₂	详情	详情
(VIII)	43906	tert-butyl 4-([[(4-nitrobenzyl)oxy]carbonyl]amino)-1-piperidinecarboxylate		C₁₈H₂₅N₃O₆	详情	详情
(IX)	13235	Allyl chloride; 3-Chloro-1-propene	107-05-1	C₃H₅Cl	详情	详情

Extended Information