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【结 构 式】

【分子编号】48152

【品名】3,4-dihydro-2H-1,4-benzoxazine

【CA登记号】

【 分 子 式 】C8H9NO

【 分 子 量 】135.1656

【元素组成】C 71.09% H 6.71% N 10.36% O 11.84%

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:(I)

Nitrosation of dihydrobenzoxazine (I) with NaNO2 and HOAc, followed by LiAlH4 reduction of the resulting N-nitroso derivative (II), furnished hydrazine (III). Subsequent Fischer indole cyclization of hydrazine (III) with piperidone hydrate (IV) under acidic conditions afforded the tetracyclic system (V). The pyrrole ring double bond of (V) was then reduced employing NaBH3CN and CF3COOH to provide the racemic cis-tetracycle (VI). Resolution of (VI) was carried out by preparative chiral HPLC of the corresponding N-Boc derivative. The desired N-Boc enantiomer (VII) was then deprotected by acidic treatment to give the chiral secondary amine (VIII). This was finally alkylated with 2'-amino-4-chloro-4'-fluorobutyrophenone (IX) to yield the title compound.

1 Boyle, K.E.; Robichaud, A.J.; Lee, T.; et al.; Novel, highly potent and selective serotonin 5-HT2A/dopamine D2 receptor antagonists as potential antipsychotics. 221st ACS Natl Meet (April 1 2001, San Diego) 2001, Abst MEDI 98.
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) 48152 3,4-dihydro-2H-1,4-benzoxazine C8H9NO 详情 详情
(II) 48153 4-nitroso-3,4-dihydro-2H-1,4-benzoxazine C8H8N2O2 详情 详情
(III) 48154 2,3-dihydro-4H-1,4-benzoxazin-4-amine; 2,3-dihydro-4H-1,4-benzoxazin-4-ylamine C8H10N2O 详情 详情
(IV) 18178 4,4-piperidinediol 73390-11-1 C5H11NO2 详情 详情
(V) 48155 1,2,7,8,9,10-hexahydro[1,4]oxazino[2,3,4-hi]pyrido[4,3-b]indole C13H14N2O 详情 详情
(VI) 48156 1,2,6b,7,8,9,10,10a-octahydro[1,4]oxazino[2,3,4-hi]pyrido[4,3-b]indole C13H16N2O 详情 详情
(VII) 48157 tert-butyl (6bR,10aS)-1,2,6b,9,10,10a-hexahydro[1,4]oxazino[2,3,4-hi]pyrido[4,3-b]indole-8(7H)-carboxylate C18H24N2O3 详情 详情
(VIII) 48158 (6bR,10aS)-1,2,6b,7,8,9,10,10a-octahydro[1,4]oxazino[2,3,4-hi]pyrido[4,3-b]indole C13H16N2O 详情 详情
(IX) 48151 1-(2-amino-4-fluorophenyl)-4-chloro-1-butanone C10H11ClFNO 详情 详情
Extended Information