Ethylene Glycol → HCID 86689016, compound

Participants

Role	Name	HCID	Charge
Reactant	Ethylene Glycol	HCID 174	—
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	3-(4-Tert-butylphenoxy)azetidine	HCID 53409561	—
Reactant	N-[(1S)-1-(4-iodophenyl)ethyl]acetamide	HCID 66634778	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Isopropanol	HCID 3776	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	HCID 86689016	HCID 86689016	—

Reaction Conditions

Temperature	80 °C

Reaction Steps

Under an argon atmosphere a mixture of 0.28 g (0.97 mmol) (S)—N-[1-(4-iodo-phenyl)-ethyl]-acetamide (III.1), 0.20 g (0.98 mmol) 3-(4-tert-butyl-phenoxy)-azetidine, 0.0093 g (0.049 mmol) CuI, 0.41 g (1.95 mmol) K3PO4 and 0.12 g (1.95 mmol) ethyleneglycol in 1.0 mL isopropanol is stirred for 12 h at 80° C. 100 mL Ethyl acetate are added and the mixture is washed with ammonia solution (5%, 2×). The aq. layer is extracted with ethyl acetate (1×) and the combined organic layers are dried (MgSO4) and concentrated in vacuo. The residue is purified by HPLC (XBridge, MeOH/water (+0.3% NH4OH)) to yield the desired product.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08530461B2
Source dataset	uspto-grants-2013_09
ORD ID	ord-bd90f25b2453494399af60cbdbec2fea
Source note	uspto-grants-2013_09