Benzyl Bromide → 1-Benzyl-4-[3-methyl-1-(3-phenyl-propyl)-1H-indole-6-yl]-pyrrolidine-2-one

HRID 392193ノート

反応式

HRID 392193 の反応式
[H-].[Na+].[CH3:3][C:4]1[C:12]2[C:7](=[CH:8][C:9]([CH:13]3[CH2:17][NH:16][C:15](=[O:18])[CH2:14]3)=[CH:10][CH:11]=2)[N:6]([CH2:19][CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:5]=1.[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.CN1C(=O)N(C)CCC1>O1CCCC1>[CH2:28]([N:16]1[CH2:17][CH:13]([C:9]2[CH:8]=[C:7]3[C:12]([C:4]([CH3:3])=[CH:5][N:6]3[CH2:19][CH2:20][CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[CH:11][CH:10]=2)[CH2:14][C:15]1=[O:18])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

参加物

6

反応物 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 226634514-[3-methyl-1-(3-phenyl-propyl)-1H-indole-6-yl]-pyrrolidine-2-one

生成物 1

HCID 226633041-Benzyl-4-[3-methyl-1-(3-phenyl-propyl)-1H-indole-6-yl]-pyrrolidine-2-one収率 77.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of sodium hydride (0.013 g) in tetrahydrofuran at 0° C., under argon, was treated with a solution of 4-[3-methyl-1-(3-phenyl-propyl)-1H-indole-6-yl]-pyrrolidine-2-one (0.184 g, Example 20) and benzyl bromide (0.094 g) in dry tetrahydrofuran. The mixture was allowed to warm to room temperature then treated with N,N′-dimethylpropyleneurea (0.05 g). After stirring at room temperature overnight the solution was partitioned between ethyl acetate (15 ml)and 1N hydrochloric acid (15 ml). The organic phase was dried over magnesium sulphate then evaporated. The residue was subjected to preparative layer chromatography on silica using a mixture of ethyl acetate and hexane (3:7, v/v) as eluent to yield the title compound (0.18 g) as an oil. [Elemental analysis:— C, 79.16; H, 6.98; N, 6.14%. Calculated for C29H30N2O.H2O:— C, 79.04; H, 7.33; N, 6.36%].

後処理

  1. customwas partitioned between ethyl acetate (15 ml)and 1N hydrochloric acid (15 ml)
  2. dry with materialThe organic phase was dried over magnesium sulphate
  3. customthen evaporated
  4. additiona mixture of ethyl acetate and hexane (3:7, v/v) as eluent

出典と根拠

ORDレコード
ord-3e43a644194c4e91a83ad9b68f7b1a6a
出典データセット
uspto-grants-2004_10
特許番号
US06800645B1

反応ノート

読み込み中…