Dimethylformamide → HCID 68492108, compound

HRID 21253Notes

Reaction equation

HRID 21253 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:20]=[CH:21][C:22]=1[CH:23]([O:26][CH3:27])[O:24][CH3:25])[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:39]=[O:40])C>C1COCC1>[CH3:1][O:2][CH2:3][O:4][C:5]1[C:22]([CH:23]([O:26][CH3:27])[O:24][CH3:25])=[CH:21][CH:20]=[C:7]2[C:6]=1[CH:39]([OH:40])[N:10]([C:11]([CH3:19])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:12])[C:8]2=[O:9]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 68492039HCID 68492039, compound

Product 1

HCID 68492108HCID 68492108, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar manner to Step 2 of Example 16, 3-methoxymethoxy-4-dimethoxymethyl-N-(1-methyl-1-phenylethyl)benzamide (3.61 g, 9.67 mmol) was dissolved in THF (100 mL), and the solution was treated with TMEDA (4.70 mL, 31.0 mmol), sec-butyl lithium-hexane solution (1.03 mol/L, 30.0 mL, 30.9 mmol) and DMF (1.65 mL, 21.3 mmol), followed by purification by slurry using chloroform and hexane to obtain 4-methoxymethoxy-5-dimethoxymethyl-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone (2.95 g, yield 85%).

Workup

  1. customfollowed by purification by slurry

Sources & evidence

ORD record
ord-bd120103e172485fb35919c3c6e7f97f
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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