Dimethylformamide → 4-Methoxy-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone

HRID 21075

반응식

HRID 21075 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[C:6]([NH:8][C:9]([CH3:17])([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:10])=[O:7].CN(CCN(C)C)C.C([Li])(CC)C.CCCCCC.CN([CH:43]=[O:44])C>C1COCC1>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][CH:18]=[C:5]2[C:4]=1[CH:43]([OH:44])[N:8]([C:9]([CH3:17])([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH3:10])[C:6]2=[O:7].[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:18]([CH:43]([OH:44])[N:8]([C:9]([CH3:17])([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH3:10])[C:6]2=[O:7])=[CH:19][CH:20]=1

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 474447523-methoxy-N-(1-methyl-1-phenylethyl)benzamideHCID 178444656HCID 178444656, 화합물

생성물 2

HCID 684886364-Methoxy-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone수율 66%HCID 684907896-Methoxy-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone수율 17%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

In a similar manner to Step 2 of Example 16, 3-methoxy-N-(1-methyl-1-phenylethyl)benzamide (6.00 g, 22.3 mmol) was dissolved in THF (240 mL), and the solution was treated with TMEDA (10.8 mL, 71.3 mmol), sec-butyllithium-hexane solution (0.99 mol/L, 72.0 mL, 71.3 mmol) and DMF (3.80 mL, 49.0 mmol), followed by purification by flash column chromatography (hexane/ethyl acetate=2/1, 1/1) to obtain 4-methoxy-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone (4.36 g, yield 66%) and 6-methoxy-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone (1.12 g, yield 17%).

후처리

  1. customfollowed by purification by flash column chromatography (hexane/ethyl acetate=2/1, 1/1)

출처 및 근거

ORD 기록
ord-8cd850c47c0343f19ddfb866a180154c
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745641B2

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