N-Hydroxyphthalimide → Di-tert-butyl [{4-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]piperidin-1-yl}methylylidene]biscarbamate

Participants

Role	Name	HCID	Charge
Reactant	N-Hydroxyphthalimide	HCID 10665	—
Reactant	Triphenylphosphine	HCID 11776	—
Reactant	Diisopropyl diazene-1,2-dicarboxylate	HCID 75555	—
Reactant	[Tert-butoxycarbonylimino-(4-hydroxy-piperidin-1-yl)-methyl]-carbamic acid tert-butyl ester	HCID 67271828	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	Di-tert-butyl [{4-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]piperidin-1-yl}methylylidene]biscarbamate	HCID 86699594	31.7%

Reaction Steps

To a mixture of N-hydroxyphthalimide (1.89 g, 11.62 mmol), di-tert-butyl [(4-hydroxypiperidin-1-yl)methylylidene]biscarbamate 63 (2.00 g, 5.81 mmol, US 2004/209921 A1) and triphenylphosphine (3.05 g, 11.62 mmol) in THF (100 mL) was added diisopropyl azodicarboxylate (2.47 mL, 12.78 mmol) slowly at room temperature. The resulting mixture was stirred at room temperature overnight and concentrated to provide a residue which was subjected to chromatography to give 64 (0.9 g) as a white solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08877743B2
Source dataset	uspto-grants-2014_11
ORD ID	ord-cda14df13aa4436c9671bd20cdf4c064
Source note	uspto-grants-2014_11