HRID21100

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID11776

Triphenylphosphine

C18H15P

HCID4077791

3-{[tert-Butyl(dimethyl)silyl]oxy}propan-1-ol

C9H22O2Si

结构：CC(C)(C)OC(=O)n1c(-c2ccc(O)c3c2C(=O)NC3)cc2cc(CN3CCCCC3)ccc21

HCID68493222

未命名化合物

HCID87147022

未命名化合物

PRODUCTS

生成物

结构：CC(C)(C)OC(=O)n1c(-c2ccc(OCCCO[Si](C)(C)C(C)(C)C)c3c2C(=O)NC3)cc2cc(CN3CCCCC3)ccc21

HCID68492386

未命名化合物

收率 53.4%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

In a similar manner to Step 1 of Example 149, 4-hydroxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (80.0 mg, 0.173 mmol) was dissolved in THF (4.0 mL), and the solution was treated with triphenylphosphine (136 mg, 0.519 mmol), 3-(tert-butyldimethylsilyloxy)propanol (0.111 mL, 0.519 mmol) and 40% DEAD-toluene solution (0.237 mL), followed by purification by preparative thin-layer chromatography (chloroform/methanol=4/1) to obtain 4-[3-(tert-butyldimethylsilyloxy)propoxy]-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (58.6 mg, yield 53%).

WORKUP

后处理

customfollowed by purification by preparative thin-layer chromatography (chloroform/methanol=4/1)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-135d13042c33496ba1370132395e9c95
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

[OH:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH2:20][N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:34].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Si:54]([O:61][CH2:62][CH2:63][CH2:64]O)([C:57]([CH3:60])([CH3:59])[CH3:58])([CH3:56])[CH3:55].CCOC(/N=N/C(OCC)=O)=O.C1(C)C=CC=CC=1>C1COCC1>[Si:54]([O:61][CH2:62][CH2:63][CH2:64][O:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:27]([O:29][C:30]([CH3:31])([CH3:33])[CH3:32])=[O:28])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH2:20][N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:34])([C:57]([CH3:58])([CH3:59])[CH3:60])([CH3:56])[CH3:55]