Dimethylformamide → HCID 68489666, compound

HRID 21084Notes

Reaction equation

HRID 21084 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:20]=[CH:21][CH:22]=1)[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.C([Li])(CC)C.CCCCCC.CN([CH:45]=[O:46])C>C1COCC1>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:22]=[CH:21][CH:20]=[C:7]2[C:6]=1[CH:45]([OH:46])[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

6

Reactant 4

HCID 6228DimethylformamideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 684927953-methoxymethoxy-N-(1-methyl-1-phenylethyl)benzamideHCID 178444656HCID 178444656, compound

Product 1

HCID 68489666HCID 68489666, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar manner to Step 2 of Example 16, 3-methoxymethoxy-N-(1-methyl-1-phenylethyl)benzamide (8.07 g, 27.0 mmol) was dissolved in THF (320 mL), and the solution was treated with TMEDA (13.0 mL, 85.4 mmol), sec-butyllithium-hexane solution (0.99 mol/L, 87.1 mL, 86.3 mmol) and DMF (4.60 mL, 59.3 mmol), followed by purification by slurry using hexane to obtain 4-methoxymethoxy-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone (8.50 g, yield 96%).

Workup

  1. customfollowed by purification by slurry

Sources & evidence

ORD record
ord-968b6f3269ad4bda9bf617f81df9bb28
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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