2-(3-hydroxycyclobutyl)acetonitrile synthesis

5synthesis methods

Product Name:2-(3-hydroxycyclobutyl)acetonitrile
CAS Number:1622903-17-6
Molecular formula:C6H9NO
Molecular Weight:111.14

Acetonitrile, 2-[3-(phenylmethoxy)cyclobutylidene]-

1187595-82-9
2 suppliers
inquiry

1622903-17-6
2 suppliers
inquiry

Yield:1622903-17-6 100%

Reaction Conditions:

with 10 wt% Pd(OH)2 on carbon;hydrogen in tetrahydrofuran at 20; under 5171.62 Torr; for 2.5 h;Inert atmosphere;

Steps:

50 2-(3-hydroxycyclobutyl)acetonitrile

Palladium hydroxide on carbon (20% Pd, wet, 430 mg) was added to a solution of 2-(3-(benzyloxy)cyclobutylidene)acetonitrile (Preparation 49, 430 mg, 2.16 mmol) in THF (6.5 mL). The mixture was pressurized under hydrogen (100 psi) in a steel reactor and stirred at about 20° C. for about 1 hr. Additional palladium hydroxide on carbon (20% Pd, wet, 430 mg) added and the mixture was re-pressurized under hydrogen (100 psi) and stirred for about 1.5 hrs longer. The mixture was diluted with EtOAc, filtered through Celite, and the filtrate was concentrated to afford the title compound as a colorless oil (240 mg, 100%) as a mixture of cis and trans isomers.Isomer 1-(400 MHz, CDCl₃) δ: 4.52 (quin, 1H), 2.63-2.74 (m, 2H), 2.19-2.28 (m, 4H), 2.07-2.17 (m, 1H), 1.83 (br. s, 1H).Isomer 2: ¹H NMR (400 MHz, CDCl₃) δ: 4.14-4.25 (m, 1H), 2.55-2.64 (m, 2H), 2.48 (dd, 4H), 1.83 (br. s, 1H), 1.67-1.79 (m, 1H).

References:

US2017/240552,2017,A1 Location in patent:Paragraph 0391; 0392; 0393; 0394