4-AMINOISOINDOLIN-1-ONE → HCID 11166408, compound

HRID 1444428Notes

Reaction equation

HRID 1444428 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([C:10]([CH3:21])([CH3:20])[CH2:11][C:12]([OH:19])([C:15]([F:18])([F:17])[F:16])[CH:13]=O)[C:4]=2[O:3][CH2:2]1.[NH2:22][C:23]1[CH:31]=[CH:30][CH:29]=[C:28]2[C:24]=1[CH2:25][NH:26][C:27]2=[O:32]>C(O)(=O)C>[OH:19][C:12]1([C:15]([F:16])([F:17])[F:18])[CH2:11][C:10]([CH3:20])([CH3:21])[C:9]2[C:4]3[O:3][CH2:2][O:1][C:5]=3[CH:6]=[CH:7][C:8]=2[CH:13]1[NH:22][C:23]1[CH:31]=[CH:30][CH:29]=[C:28]2[C:24]=1[CH2:25][NH:26][C:27]2=[O:32]

Participants

4

Reactant 2

HCID 98555134-AMINOISOINDOLIN-1-ONEHCID 17989281HCID 17989281, compound

Product 1

HCID 11166408HCID 11166408, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

800 mg (2.63 mmol) of 4-(1,3-benzodioxol-4-yl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal is stirred in 5.2 ml of glacial acetic acid with 389 mg (2.63 mmol) of 4-amino-2,3-dihydroisoindol-1-one overnight at room temperature. The reaction mixture is spun in until a dry state is reached, and the residue is chromatographed on a Flashmaster. 725 mg (62.8%) of the desired compound is isolated as a racemate. Racemate cleavage (Chiralpak AD 20μ; mobile solvent: hexane/ethanol/diethylamine) yields 279.2 mg of the (+)-enantiomer {[α]D=+20.7 (c=1.03, methanol)}and 297.5 mg of the (−)-enantiomer {[α]D=−23.4 (c=1.02, methanol)}

Workup

  1. customthe residue is chromatographed on a Flashmaster

Sources & evidence

ORD record
ord-c67a8e5b8faf481bbfcf2529e3d9c1b2
Source dataset
uspto-grants-2010_02
Patent number
US07662821B2

Reaction notes

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