Dimethylformamide → tert-Butyl 4-cyanophenethylcarbamate

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	[2-(4-Bromo-phenyl)ethyl]-carbamic acid tert-butyl ester	HCID 14221818	—
Catalyst	Zinc cyanide (Zn(CN)2)	HCID 11186	—
Catalyst	HCID 178418397	HCID 178418397	—
Product	tert-Butyl 4-cyanophenethylcarbamate	HCID 21955533	31%

Reaction Conditions

Temperature	150 °C

Reaction Steps

Compound 113 (530 mg, 1.8 mmol) was dissolved in dry DMF (17 mL) under N2. Zn(CN)2 (416 mg, 3.6 mmol) and Pd(PPh3)4 (200 mg, 0.18 mmol) was added. The reaction mixture was stirred and heated at 150° C. in a microwave instrument (CEM Discover®) for 20 min and the reaction mixture was then concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with EtOAc/hexanes (20˜80%) to yield 114 (540 mg, 31%) as a white solid. MS (APCI, negative): m/z 245 [M−H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08541423B2
Source dataset	uspto-grants-2013_09
ORD ID	ord-6655b0516066424fbb705918d32a36c6
Source note	uspto-grants-2013_09