|
【结 构 式】 
|
【分子编号】62037 【品名】(2R)-3,4-dihydro-2H-chromen-2-ylmethanol 【CA登记号】 |
【 分 子 式 】C10H12O2 【 分 子 量 】164.20408 【元素组成】C 73.15% H 7.37% O 19.49% |
合成路线1
该中间体在本合成路线中的序号：(III)Racemic 3,4-dihydro-2H-1-benzopyran-2-carboxylic acid (I) is resolved into the corresponding enantiomers by recrystallization of the diastereomeric salts with (+)-(R)-alpha-methylbenzylamine, and the desired (R)-carboxylic acid is further esterified with H2SO4/EtOH to furnish the ethyl ester (II). Subsequent reduction of ester (II) with NaBH4 in toluene/EtOH leads to alcohol (III), which is converted into mesylate (IV) employing methanesulfonyl chloride and triethylamine. Mesylate (IV) is finally condensed with 1-(3-aminopropyl)-hexahydro-2-pyrimidinone (V) by heating with CaO at 100 C in THF in an autoclave to provide the title compound
| 【1】 De Bruyn, M.F.L.; Schroven, M.F.J.; Wigerinck, P.T.B.P.; Verschueren, W.G. (Janssen Pharmaceutica NV); (Benzodioxan, benzofuran or benzopyran) derivs. having fundic relaxation properties. WO 9929687 . |
| 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) | 17037 | 2-chromanecarboxylic acid | C10H10O3 | 详情 | 详情 | |
| (II) | 13885 | ethyl (2R)-3,4-dihydro-2H-chromene-2-carboxylate | C12H14O3 | 详情 | 详情 | |
| (III) | 62037 | (2R)-3,4-dihydro-2H-chromen-2-ylmethanol | C10H12O2 | 详情 | 详情 | |
| (IV) | 62038 | (2R)-3,4-dihydro-2H-chromen-2-ylmethyl methanesulfonate | C11H14O4S | 详情 | 详情 | |
| (V) | 62039 | 1-(3-aminopropyl)tetrahydro-2(1H)-pyrimidinone | C7H15N3O | 详情 | 详情 |