Category: 10444-38-9

Application of 10444-38-9,Some common heterocyclic compound, 10444-38-9, name is Ethyl 4-cyanobutanoate, molecular formula is C7H11NO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: To a solution of the cyano ethyl esters (4.8mmol) in pyridine (26ml) were added water (13ml), acetic acid (13ml), sodium hyposphite (39.06mmol) and Raney nickel. The suspension was then stirred at 40C for 2hr. The catalyst was removed by filtration, and washed with ethanol (5ml). Water (300ml) and diethyl ether (80ml) were added to the filtrate, and the organic layer was separated. The aqueous phase was further extracted with diethyl ether (2x80ml), and the combined extracts were washed with water (300ml), and brine (100ml), and dried over Na2SO4 anhydrous, concentrated under vacuo, and the residue was purified by silica gel dry column vacuum chromatography ( DCVC) by stepwise gradient elution with dichloromethane/hexane (50:50 to 100:0).

The synthetic route of 10444-38-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE UNIVERSITY OF SYDNEY; UNIVERSITY OF TECHNOLOGY SYDNEY; VANDENBERG, Robert; RYAN, Renae Monique; RAWLING, Tristan; IMLACH, Wendy; CHRISTIE, Macdonald; CARLAND, Jane; MOSTYN, Shannon; (169 pag.)WO2018/132876; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

10444-38-9, name is Ethyl 4-cyanobutanoate, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. COA of Formula: C7H11NO2

General procedure: A 1 M solution of LiHMDS in THF (5.1 eq) was added slowly to a solution of NH2OBn.HCl (1.1 eq.) in THF (4 mL/mmol) at -78C. The mixture was stirred 30 min before the addition of the nitrile (1 eq). After total consumption of the starting materials (TLC), the reaction was quenched with a saturated aqueous solution of NH4Cl, warmed up to room temperature, and extracted three times with AcOEt. The collected organic layers were dried over Na2SO4, filtered and evaporated to dryness under reduced pressure.

The synthetic route of 10444-38-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nguyen-Trung, Anh Thu; Tritsch, Denis; Grosdemange-Billiard, Catherine; Rohmer, Michel; Bioorganic and Medicinal Chemistry Letters; vol. 23; 6; (2013); p. 1643 – 1647;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 10444-38-9, These common heterocyclic compound, 10444-38-9, name is Ethyl 4-cyanobutanoate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

PREPARATION 1 Ethyl 4-(1H-tetrazole-5-yl)butanoate Ethyl 4-cyanobutyrate (approximately 15 g) was dissolved in DME. Tris(n-butyl)tin azide (5 ml) was added and the reaction solution was heated to 85 overnight then cooled to room temperature. The cooled solution was diluted with methanol (20 ml) then 1N hydrochloric acid (20 ml) was added. The solution was stirred for one hour then partitioned between ethyl acetate and water. The organic layer was separated, dried over magnesium sulfate and evaporated under reduced pressure. The residue was chromatographed by preparatory-scale HPLC (silcia column) eluted with a gradient of 30 to 70% ethyl acetate in hexane plus 1% acetic and to yield 3.39 g of the title product: n.m.r.(300 MHz, CDCl3) delta: 4.2 (q, 2H); 2.95 (t, 2H); 2.5 (t, 2H); 2.1 (t, 2H); 1.3 (t, 3H).

The synthetic route of 10444-38-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eli Lilly and Company; US4820723; (1989); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts