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【结 构 式】

【分子编号】58485

【品名】benzyl 4-benzyl-4-hydroxy-1-piperidinecarboxylate

【CA登记号】

【 分 子 式 】C20H23NO3

【 分 子 量 】325.40756

【元素组成】C 73.82% H 7.12% N 4.3% O 14.75%

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:(II)

Acylation of 4-benzyl-4-hydroxypiperidine (I) by means of benzyl chloroformate provides carbamate (II). Subsequent dehydration of the tertiary alcohol group of (II) employing SOCl2 and pyridine leads to the tetrahydropyridine (III). Oxidation of tetrahydropyridine (III) with m-chloroperbenzoic acid gives epoxide (IV) which, upon acidic hydrolysis, is converted to the trans-diol (V). Resolution of the racemic diol (V) is performed via esterification with (S)-N-trifluoroacetylproline chloride (VI), followed by chromatographic separation of the resultant diastereomeric esters. The desired isomer (VII) is then hydrolyzed under basic conditions to yield the (R,R)-diol (VIII). Removal of the N-carbobenzoxy group of (VIII) by hydrogenolysis leads to (R,R)-4-benzyl-3,4-dihydroxypiperidine (IX), which is alkylated by the alkyl chloride (X) to produce (XI). Finally, hydrogenolysis of the benzyl ether group of (XI) furnishes the title compound.

1 Wyler, R.; Buettelmann, B.; Alanine, A.; Pinard, E.; Jaeschke, G.; Neidhart, M.-P. (Hoffmann-La Roche, Inc.); Neuroprotective substd. piperidine cpds. with activity as NMDA NR2B subtype selective antagonists. US 6432985; WO 0181309 .
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) 58484 4-benzyl-4-piperidinol; 4-Benzyl-4-hydroxypiperidine 51135-96-7 C12H17NO 详情 详情
(II) 58485 benzyl 4-benzyl-4-hydroxy-1-piperidinecarboxylate C20H23NO3 详情 详情
(III) 58486 benzyl 4-benzyl-3,6-dihydro-1(2H)-pyridinecarboxylate C20H21NO2 详情 详情
(IV) 58487 benzyl 6-benzyl-7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate C20H21NO3 详情 详情
(V) 58488 benzyl (3R,4R)-4-benzyl-3,4-dihydroxy-1-piperidinecarboxylate C20H23NO4 详情 详情
(VI) 55850 (5S)-5-(aminomethyl)-3-(4-{4-[2-(benzyloxy)acetyl]-1-piperazinyl}-3-fluorophenyl)-1,3-oxazolidin-2-one C23H27FN4O4 详情 详情
(VII) 58489 (2S)-1-(2,2,2-trifluoroacetyl)-2-pyrrolidinecarbonyl chloride C7H7ClF3NO2 详情 详情
(VIII) 58490 benzyl (3R,4R)-4-benzyl-4-hydroxy-3-({[(2S)-1-(2,2,2-trifluoroacetyl)pyrrolidinyl]carbonyl}oxy)-1-piperidinecarboxylate C27H29F3N2O6 详情 详情
(IX) 58491 (3R,4R)-4-benzyl-3,4-piperidinediol C12H17NO2 详情 详情
(X) 58492 1-(benzyloxy)-4-(2-chloroethoxy)benzene; benzyl 4-(2-chloroethoxy)phenyl ether C15H15ClO2 详情 详情
(XI) 58493 (3R,4R)-4-benzyl-1-{2-[4-(benzyloxy)phenoxy]ethyl}-3,4-piperidinediol C27H31NO4 详情 详情
Extended Information