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

HRID 21275Notes

Reaction equation

HRID 21275 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:20]=[CH:21][C:22]=1[CH3:23])[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:35]=[O:36])C>C1COCC1>[CH3:1][O:2][CH2:3][O:4][C:5]1[C:22]([CH3:23])=[CH:21][CH:20]=[C:7]2[C:6]=1[CH:35]([OH:36])[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 684929793-methoxymethoxy-4-methyl-N-(1-methyl-1-phenylethyl)benzamide

Product 1

HCID 684937864-Methoxymethoxy-5-methyl-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinoneYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar manner to Step 2 of Example 16, 3-methoxymethoxy-4-methyl-N-(1-methyl-1-phenylethyl)benzamide (3.40 g, 10.9 mmol) was dissolved in THF (130 mL), and the solution was treated with TMEDA (5.20 mL, 34.5 mmol), sec-butyl lithium-hexane solution (0.95 mol/L, 36.5 mL, 34.7 mmol) and DMF (1.85 mL, 23.9 mmol), followed by purification by flash column chromatography (hexane/ethyl acetate=4/1 to 7/3 to 6/4). The obtained solid was purified by slurry using isopropylether and hexane to obtain 4-methoxymethoxy-5-methyl-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone (2.96 g, yield 80%).

Workup

  1. customfollowed by purification by flash column chromatography (hexane/ethyl acetate=4/1 to 7/3 to 6/4)
  2. customThe obtained solid was purified by slurry

Sources & evidence

ORD record
ord-309f6d84eeea4300b7d2dc816a4dcab5
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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