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【结 构 式】

【分子编号】38424

【品名】(2S)-Spiro[benzo[C]thiophene-1(3H),4'-piperidine]-1'-carboxylic acid, 1,1-dimethylethyl ester, 2-oxide

【CA登记号】191673-21-9

【 分 子 式 】C17H23NO3S

【 分 子 量 】321.44056

【元素组成】C 63.52% H 7.21% N 4.36% O 14.93% S 9.98%

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:(V)

Lithiation of 2-bromobenzyl thiol (I) followed by addition to N-Boc-4-piperidone (II) gave mercapto alcohol (III), which was cyclized to the spiro derivative by refluxing in 4N sulfuric acid. Protection as the tert-butyl carbamate (IV), followed by oxidation with m-chloroperbenzoic acid produced sulfoxide (V). After acid cleavage of the Boc protecting group of (V), resolution with (S)-(+)-mandelic acid furnished the required (S)-enantiomer (VII). Alternatively, asymmetric oxidation of sulfide (IV) with (3'S,2R)-(-)-N-(phenylsulfonyl)(3,3-dichlorocamphoryl)oxaziridine produced the (S)-sulfoxide (VI), which was further deprotected to (VII) with HCl in dioxan.

1 Kurata, H.; Ito, K.; Nakajima, K.; Yamaguchi, T.; Ishibashi, K.; Fukuzawa, T.; Nishi, T. (Sankyo Co., Ltd.); Azaheterocyclic cpds. having tachykinin receptor antagonist activity; NK1 and NK2. EP 0776893; JP 1998152478; JP 1998182649; JP 1998182650 .
2 Nishi, T.; Yamaguchi, T. (Sankyo Co., Ltd.); Salts of optically active sulfoxide deriv.. EP 0987269; JP 1999043490; WO 9854191 .
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) 38421 (2-bromophenyl)methanethiol; 2-bromobenzylhydrosulfide C7H7BrS 详情 详情
(II) 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
(III) 38422 tert-butyl 4-hydroxy-4-[2-(sulfanylmethyl)phenyl]-1-piperidinecarboxylate C17H25NO3S 详情 详情
(IV) 38423 Spiro[benzo[C]thiophene-1(3H),4'-piperidine]-1'-carboxylic acid, 1,1-dimethylethyl ester 173944-03-1 C17H23NO2S 详情 详情
(V) 38424 (2S)-Spiro[benzo[C]thiophene-1(3H),4'-piperidine]-1'-carboxylic acid, 1,1-dimethylethyl ester, 2-oxide 191673-21-9 C17H23NO3S 详情 详情
(VI) 38425 Spiro[benzo[C]thiophene-1(3H),4'-piperidine]-1'-carboxylic acid, 1,1-dimethylethyl ester, 2-oxide 173944-04-2 C17H23NO3S 详情 详情
(VII) 38426 (2S)-Spiro[benzo[C]thiophene-1(3H),4'-piperidine] 2-oxide 191673-15-1 C12H15NOS 详情 详情
Extended Information