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【结 构 式】 
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【分子编号】43391 【品名】methyl 3-[(3S)piperidinyl]phenyl sulfone; (3S)-3-[3-(methylsulfonyl)phenyl]piperidine 【CA登记号】 |
【 分 子 式 】C12H17NO2S 【 分 子 量 】239.33852 【元素组成】C 60.22% H 7.16% N 5.85% O 13.37% S 13.4% |
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)The condensation of 3-(methylsulfonyl)bromobenzene (I) with diethyl(3-pyridyl)borane (II) by means of Pd(PPh3)4, KOH and tetrabutylammonium iodide (TBAI) gives 3-[3-(methylsulfonyl)phenyl]pyridine (III), which is hydrogenated with H2 over PtO2 in methanol, yielding the racemic piperidine (IV). The optical resolution of (IV) with (+)-tartaric acid affords the (S)-enantiomer (V), which is alkylated by reductocondensation with propionic aldehyde and NaBH(O-tBu)3 in dichloroethane and HOAc.
| 【1】 Sonesson, C.; Lindborg, J.; An efficient synthesis of the novel dopamine autoreceptor antagonist S-(-)-OSU6162, via Palladium catalyzed cross-coupling reaction. Tetrahedron Lett 1994, 35, 48, 9063. |
| 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) | 43388 | (3-bromophenyl)(methyl)dioxo-lambda(6)-sulfane; 3-bromophenyl methyl sulfone | C7H7BrO2S | 详情 | 详情 | |
| (II) | 20086 | 3-(diethylboryl)pyridine | C9H14BN | 详情 | 详情 | |
| (III) | 43389 | methyl 3-(3-pyridinyl)phenyl sulfone; 3-[3-(methylsulfonyl)phenyl]pyridine | C12H11NO2S | 详情 | 详情 | |
| (IV) | 43390 | methyl 3-(3-piperidinyl)phenyl sulfone; 3-[3-(methylsulfonyl)phenyl]piperidine | C12H17NO2S | 详情 | 详情 | |
| (V) | 43391 | methyl 3-[(3S)piperidinyl]phenyl sulfone; (3S)-3-[3-(methylsulfonyl)phenyl]piperidine | C12H17NO2S | 详情 | 详情 | |
| (VI) | 15966 | propionaldehyde | 123-38-6 | C3H6O | 详情 | 详情 |
Extended Information