2-(2-Methoxyethoxy)-1H-isoindole-1,3(2H)-dione → tert-butyl N-(2-(aminooxy)ethyl)carbamate

Reaction equation

O=C1C2C(=CC=CC=2)C(=O)[N:3]1[O:12][CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19].COCCON1C(=O)C2C(=CC=CC=2)C1=O>>[NH2:3][O:12][CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:20])([CH3:19])[CH3:21]

Participants

Reactant 2

HCID 129191152-(2-Methoxyethoxy)-1H-isoindole-1,3(2H)-dione

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

Product 1

HCID 15610443tert-butyl N-(2-(aminooxy)ethyl)carbamateYield 58%

Procedure

2E was deprotected as previously described in 2A, Step 2 to give tert-butyl 2-(aminooxy)ethylcarbamate (2F, 1.26 g, 58% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.45 (s, 9H) 3.37 (q, J=5.31 Hz, 2H) 3.62-3.85 (m, 2H) 4.90 (br. s., 1H) 5.47 (br. s., 2H).

Sources & evidence

ORD record: ord-2b1e0ddd95614fd19e7ba49713a87d9d
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071766B2

Reaction notes

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