N-Hydroxyphthalimide → tert-Butyl (2-((1,3-dioxoisoindolin-2-yl)oxy)ethyl)carbamate

Reaction equation

[OH:1][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].O[N:13]1[C:17](=[O:18])[C:16]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]2[C:14]1=[O:23]>>[O:23]=[C:14]1[C:15]2[C:16](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17](=[O:18])[N:13]1[O:1][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:10])[CH3:9]

Participants

Reactant 2

HCID 10665N-Hydroxyphthalimide

HCID 2733206tert-butyl N-(2-hydroxyethyl)carbamate

Product 1

HCID 18929164tert-Butyl (2-((1,3-dioxoisoindolin-2-yl)oxy)ethyl)carbamate

Procedure

tert-Butyl 2-(1,3-dioxoisoindolin-2-yloxy)ethylcarbamate 2E was prepared with quantitative yield from tert-butyl 2-hydroxyethylcarbamate and N-hydroxyphthalimide by a procedure analogous to Example 2A, Step 1. ESI-MS: m/z 329.3 (M+Na)+.

Sources & evidence

ORD record: ord-d5d1761b8c824159a8cea9148ccdb69c
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071766B2

Reaction notes

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