(S)-3-[1-(1,3-dioxo-1,3-dihydroisoindol-2-yl)isoquinolin-6-yloxy]piperidine-1-carboxylic acid tert-butyl ester → Phthalimide

HRID 1435971Notes

Reaction equation

HRID 1435971 reaction equation
C(OC(N1CCC[C@H](OC2C=C3C(=CC=2)C([N:25]2[C:33](=[O:34])[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[C:26]2=[O:35])=NC=C3)C1)=O)(C)(C)C>ClCCl.FC(F)(F)C(O)=O>[C:26]1(=[O:35])[C:27]2[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:33](=[O:34])[NH:25]1

Participants

4

Reactant 1

HCID 68874394(S)-3-[1-(1,3-dioxo-1,3-dihydroisoindol-2-yl)isoquinolin-6-yloxy]piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 6809PhthalimideYield 293.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of (S)-3-[1-(1,3-dioxo-1,3-dihydroisoindol-2-yl)isoquinolin-6-yloxy]piperidine-1-carboxylic acid tert-butyl ester (340 mg) in dichloromethane (14 ml) and trifluoroacetic acid (2.8 ml) was stirred at ambient temperature for 1 h. The mixture was concentrated in vacuo then flash chromatography of the residue on silica (eluent: 2-10% methanol in dichloromethane) gave (S)-2-(6-piperidin-3-yloxy)isoquinolin-1-yl]isoindole-1,3-dione (310 mg), EIMS: m/z=374.3 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-ce30a600eaff4e4e857b7469da6a1c9f
Source dataset
uspto-grants-2009_11
Patent number
US07618985B2

Reaction notes

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