Dimethylformamide → HCID 68491896, compound

HRID 21258Notes

Reaction equation

HRID 21258 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[O:20][CH2:21][O:22][CH3:23])[C:5]([NH:7][C:8]([CH3:16])([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:9])=[O:6].CN(CCN(C)C)C.CN([CH:35]=[O:36])C>C1COCC1>[Cl:1][C:2]1[C:19]([O:20][CH2:21][O:22][CH3:23])=[CH:18][CH:17]=[C:4]2[C:3]=1[CH:35]([OH:36])[N:7]([C:8]([CH3:16])([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:9])[C:5]2=[O:6]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 684890703-chloro-4-methoxymethoxy-N-(1-methyl-1-phenylethyl)benzamide

Product 1

HCID 68491896HCID 68491896, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar manner to Step 2 of Example 16, 3-chloro-4-methoxymethoxy-N-(1-methyl-1-phenylethyl)benzamide (2.83 g, 8.48 mmol) was dissolved in THF (110 mL), and the solution was treated with TMEDA (4.10 mL, 27.2 mmol), sec-butyl lithium-hexane solution (1.01 mol/L, 27.0 mL, 27.2 mmol) and DMF (1.40 mL, 18.1 mmol), followed by purification by flash column chromatography (chloroform/methanol=100/0 to 97/3) to obtain 4-chloro-5-methoxymethoxy-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone (3.01 g, yield 98%).

Workup

  1. customfollowed by purification by flash column chromatography (chloroform/methanol=100/0 to 97/3)

Sources & evidence

ORD record
ord-941472ff682f42a9802c9787091ea640
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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