Dimethylformamide → 4-Methoxymethoxy-5-methoxy-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone

HRID 21269Notes

Reaction equation

HRID 21269 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[C:8]([NH:10][C:11]([CH3:19])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:12])=[O:9].CN(CCN(C)C)C.CN([CH:36]=[O:37])C>C1COCC1>[CH3:1][O:2][CH2:3][O:4][C:5]1[C:22]([O:23][CH3:24])=[CH:21][CH:20]=[C:7]2[C:6]=1[CH:36]([OH:37])[N:10]([C:11]([CH3:19])([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH3:12])[C:8]2=[O:9]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 68492049HCID 68492049, compound

Product 1

HCID 684927044-Methoxymethoxy-5-methoxy-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinoneYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar manner to Step 2 of Example 16, 3-methoxymethoxy-4-methoxy-N-(1-methyl-1-phenylethyl)benzamide (7.50 g, 22.8 mmol) was dissolved in THF (200-mL), and the solution was treated with TMEDA (11.0 mL, 72.9 mmol), sec-butyl lithium-hexane solution (0.95 mol/L, 77.0 mL, 73.2 mmol) and DMF (3.88 mL, 50.1 mmol), followed by purification by slurry using isopropylether and hexane to obtain 4-methoxymethoxy-5-methoxy-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone (6.41 g, yield 79%).

Workup

  1. customfollowed by purification by slurry

Sources & evidence

ORD record
ord-b43be227275b472386334421439f6d50
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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