Phthalimide → HCID 86705515, compound

HRID 2279517Notes

Reaction equation

HRID 2279517 reaction equation
C(OC(N1CCC[C@@H]1C(O)=O)=O)(C)(C)C.[Cl:16][C:17]1[CH:18]=[C:19]([CH:34]=[CH:35][C:36]=1[Cl:37])[C:20]([C@H:22]1[CH2:26][CH2:25][CH2:24][N:23]1[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=O.BrC1C=CC(Cl)=C(Cl)C=1.CB1N2CCC[C@@H]2C(C2C=CC=CC=2)(C2C=CC=CC=2)O1.[C:68]1(=[O:78])[C:76]2[C:71](=[CH:72][CH:73]=[CH:74][CH:75]=2)[C:70](=[O:77])[NH:69]1>>[Cl:16][C:17]1[CH:18]=[C:19]([C@H:20]([N:69]2[C:70](=[O:77])[C:71]3[C:76](=[CH:75][CH:74]=[CH:73][CH:72]=3)[C:68]2=[O:78])[C@H:22]2[CH2:26][CH2:25][CH2:24][N:23]2[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH:34]=[CH:35][C:36]=1[Cl:37]

Participants

6

Reactant 5

HCID 6809PhthalimideHCID 290134-Bromo-1,2-dichlorobenzeneHCID 688022(2R)-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acidHCID 9838490(R)-2-Methyl-CBS-oxazaborolidineHCID 86705516HCID 86705516, compound

Product 1

HCID 86705515HCID 86705515, compound

Procedure

(R)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid and be converted to (R)-tert-butyl 2-(3,4-dichlorobenzoyl)-pyrrolidine-1-carboxylate in accord with steps 1 and 2 of example 11, except in step 2,4-bromo-1-(trifluoromethyl)benzene was replaced with 1-bromo-3,4-dichlorobenzene. Reduction of the ketone with (R)-1-methyl-3,3-diphenylhexahydropyrrolo[1,2-c][1,3,2]oxazaborole and condensation with isoindoline-1,3 dione can be carried out in accord with procedures in steps 4 and 5 of example 11 to afford (R)-tert-butyl 2-((S)-(3,4-dichlorophenyl)(1,3-dioxoisoindolin-2-yl)methyl)pyrrolidine-1-carboxylate (242).

Sources & evidence

ORD record
ord-25f732db103d4b029c62625ae5bf31fc
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

Loading…