N-Hydroxyphthalimide → HCID 68984945, compound

HRID 1821829Notes

Reaction equation

[C:1]([O:5][C:6](=[O:14])[N:7]([CH2:11][CH2:12][OH:13])[CH:8]([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2].O[N:16]1[C:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]2[C:17]1=[O:26]>>[C:1]([O:5][C:6](=[O:14])[N:7]([CH2:11][CH2:12][O:13][N:16]1[C:20](=[O:21])[C:19]2[C:18](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:17]1=[O:26])[CH:8]([CH3:10])[CH3:9])([CH3:3])([CH3:2])[CH3:4]

Participants

Reactant 2

HCID 10665N-Hydroxyphthalimide

HCID 21942901HCID 21942901, compound

Product 1

HCID 68984945HCID 68984945, compoundYield 57%

Procedure

Reaction of (2-hydroxyethyl)isopropylcarbamic acid tert-butyl ester with N-hydroxyphthalimide following the procedure described for Reference Example 14, except purification by column chromatography (silica gel, 75:25 hexanes/EtOAc to 50:50 hexanes/EtOAc), gave tert-butyl[2-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]ethyl]isopropylcarbamate (960 mg, 57%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 1.15-1.20 (6H, br s), 1.43 (9H, s), 3.48-3.50 (2H, s), 4.08-4.15 (1H, m), 4.25-4.28 (2H, m), 7.74-7.85 (4H m).

Workup

customdescribed for Reference Example 14, except purification by column chromatography (silica gel, 75:25 hexanes/EtOAc to 50:50 hexanes/EtOAc)

Sources & evidence

ORD record: ord-030e73194e7a44d8b819aea2c04b0082
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07608627B2

Reaction notes

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