1,3-Bis(diphenylphosphino)propane → 2-Tert-butyl 5-methyl isoindoline-2,5-dicarboxylate

HRID 1726435Notizen

Reaktionsgleichung

[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13](Br)[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CO.CS(C)=O.C[CH2:54][O:55][C:56](C)=[O:57].CCCCCC>CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:54][O:55][C:56]([C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:16]2)=[O:57]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

A mixture of 5-bromo-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (200 mg, 0.67 mmol), Pd(OAc)2 (30 mg, 0.2 equiv), DPPP (55 mg, 0.2 equiv), TEA (0.93 mL, 10 equiv) and MeOH:DMSO (1:1, 4 mL) was stirred for 16 h under CO (balloon) at 80° C. LC-MS and TLC (20% EtOAc-Hexane) showed completion of the reaction. The Reaction mixture was concentrated to remove MeOH and diluted with EtOAc (10 mL), and washed with water (2×25 mL). The organic layer was dried (Na2SO4), concentrated and purified by silica gel column chromatography (eluent=20% EtOAc-Hexane), giving pure 1,3-dihydro-isoindole-2,5-dicarboxylic acid 2-tert-butyl ester 5-methyl ester (150 mg, 81%). MS (APCI+): m/z 178.1 (MH+−Boc).

Aufarbeitung

customcompletion of the reaction
concentrationThe Reaction mixture was concentrated
customto remove MeOH
additiondiluted with EtOAc (10 mL)
washwashed with water (2×25 mL)
dry with materialThe organic layer was dried (Na2SO4)
concentrationconcentrated
custompurified by silica gel column chromatography (eluent=20% EtOAc-Hexane)

Quellen und Nachweise

ORD-Eintrag: ord-4ec37d33dd3243b082fd7b7457af1d25
Quelldatensatz: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07491794B2

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