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【结 构 式】

【分子编号】10971

【品名】(4R)-4-(3-Hydroxy-4-methoxyphenyl)tetrahydro-2H-pyrrol-2-one

【CA登记号】

【 分 子 式 】C11H13NO3

【 分 子 量 】207.22916

【元素组成】C 63.76% H 6.32% N 6.76% O 23.16%

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:(VI)

The enantioselective synthesis of the (R)-enantiomer of rolipram, which is the most active, has been published: The reaction of 3-benzyloxy-4-methoxybenzaldehyde (I) with nitromethane by means of ammonium acetate in refluxing acetic acid gives 3-benzyloxy-4-methoxy-beta-nitrostyrene (II), which is condensed with the chiral oxazolidinone (R)-3-acetyl-4-benzyl-2-oxazolidinone (III) by means of sodium bis(trimethylsilyl)amine in THF yielding 4(R)-benzyl-3-[3(R)-(3-benzyloxy-4-methoxyphenyl)-4-nitrobutyryl]-2-oxa zolidinone (IV). Hydrogenation of (IV) with H2 over Raney Ni in ethanol - ethyl acetate affords 4(R)-(3-hydroxy-4-methoxyphenyl)-2-pyrrolidinone (VI) through the intermediate benzyl ether (V). Finally, compound (VI) is etherified with cyclopentyl bromide (VII) by means of NaH in refluxing THF.

1 Schmiechen, R.; Mulzer, J.; Zuhse, R.; Enantioselective synthesis of the antidepressant rolipram by Michael addition to a nitroolefin. Angew Chem. Int Ed Engl 1992, 31, 7, 870.
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) 10966 3-(Benzyloxy)-4-methoxybenzaldehyde; 3-Benzyloxy-4-methoxybenzaldehyde 6346-05-0 C15H14O3 详情 详情
(II) 10967 trans-3-Benzyloxy-4-methoxy-beta-nitrostyrene; Benzyl 2-methoxy-5-[(E)-2-nitroethenyl]phenyl ether; 2-(Benzyloxy)-1-methoxy-4-[(E)-2-nitroethenyl]benzene 63909-29-5 C16H15NO4 详情 详情
(III) 10968 (4R)-3-Acetyl-4-benzyl-1,3-oxazolidin-2-one; (R)-(-)-3-Acetyl-4-benzyl-2-oxazolidinone 184363-65-3 C12H13NO3 详情 详情
(IV) 10969 (4R)-4-Benzyl-3-[(3S)-3-[3-(benzyloxy)-4-methoxyphenyl]-4-nitrobutanoyl]-1,3-oxazolidin-2-one C28H28N2O7 详情 详情
(V) 10970 (4R)-4-[3-(Benzyloxy)-4-methoxyphenyl]-2-pyrrolidinone C18H19NO3 详情 详情
(VI) 10971 (4R)-4-(3-Hydroxy-4-methoxyphenyl)tetrahydro-2H-pyrrol-2-one C11H13NO3 详情 详情
(VII) 10972 1-Bromocyclopentane; Cyclopentyl bromide 137-43-9 C5H9Br 详情 详情
Extended Information