HRID21308

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID176

Acetic Acid

C2H4O2

HCID31268

Pyrrolidine

C4H9N

HCID5049666

Sodium triacetoxyborohydride

C6H10BNaO6

结构：COc1cc(-c2cc3c(C=O)cccc3n2C(=O)OC(C)(C)C)c2c(c1OS(C)(=O)=O)CNC2=O

HCID86628325

未命名化合物

PRODUCTS

生成物

结构：COc1cc(-c2cc3c(CN4CCCC4)cccc3n2C(=O)OC(C)(C)C)c2c(c1OS(C)(=O)=O)CNC2=O

HCID86628328

未命名化合物

收率 35.3%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6342

Acetonitrile

C2H3N

PROCEDURE

实验过程

In a similar manner to Step 2 of Example 6, 4-methanesulfonyloxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-4-formylindol-2-yl]isoindolinone (0.299 g, 0.597 mmol) was dissolved in acetonitrile (15.0 mL), and the solution was treated with pyrrolidine (0.997 mL, 11.9 mmol), acetic acid (0.684 mL, 11.9 mmol) and sodium triacetoxyborohydride (0.633 g, 2.99 mmol), followed by purification of the residue by flash column chromatography (chloroform/methanol=3/1) to obtain 4-methanesulfonyloxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-4-(pyrrolidin-1-ylmethyl)indol-2-yl]isoindolinone (0.117 g, yield 35%).

WORKUP

后处理

customfollowed by purification of the residue by flash column chromatography (chloroform/methanol=3/1)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-d7f028aefaa048da87fa397fcb3af310
来源数据集: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07745641B2
来源说明: uspto-grants-2010_06

反应 SMILES

[CH3:1][S:2]([O:5][C:6]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([C:17]2[N:18]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:19]3[C:24]([CH:25]=2)=[C:23]([CH:26]=O)[CH:22]=[CH:21][CH:20]=3)=[C:11]2[C:7]=1[CH2:8][NH:9][C:10]2=[O:35])(=[O:4])=[O:3].[NH:36]1[CH2:40][CH2:39][CH2:38][CH2:37]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(#N)C>[CH3:1][S:2]([O:5][C:6]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([C:17]2[N:18]([C:28]([O:30][C:31]([CH3:33])([CH3:34])[CH3:32])=[O:29])[C:19]3[C:24]([CH:25]=2)=[C:23]([CH2:26][N:36]2[CH2:40][CH2:39][CH2:38][CH2:37]2)[CH:22]=[CH:21][CH:20]=3)=[C:11]2[C:7]=1[CH2:8][NH:9][C:10]2=[O:35])(=[O:4])=[O:3]