Tetrahedron p. 5573 - 5582 (1988)
Update date:2022-07-29
Topics: Reduction Hydrolysis Isolation and Purification Starting Material Amination Racemization
Effenberger, Franz
Zoller, Gerhard
The alkoxide-catalyzed addition of alcohols 2 to α-chloroacrylonitrile (1) at -35 degC gives rise to 3-alkoxy-2-chloropropanenitriles 3; at 0-5 degC with excess 2 alkyl 3-alkoxy-2-chloropropanimidates 4 are obtained.The yields of 3 or 4 decrease with increasing pKa values of the alcohols 2.In the basecatalyzed addition of phenols 5 to 1, a temperature-dependent addition equilibrium is set up in which the position of equilibrium is shifted in favour of the addition products 6 with increasing pKa values of 5.The 3-alkoxy-2-chloropropanoates 8, which are readily accessible by hydrolysis of 4, react smoothly with sodium azide in the presence of a phase transfer catalyst to furnish the 3-alkoxy-2-azidopropanoates 10.Starting from benzyl 2-azido-3-benzyloxy-propanoate (10b), the specific syntheses of DL-serine (14), DL-serine hydrochloride (14*HCl), DL-serine methyl ester hydrochloride (13a*HCl), O-benzyl-DL-serine (12b), and O-benzyl-DL-serine benzyl ester hydrochloride (11b*HCl) are possible by variation of the hydrogenation conditions.
View MoreSHIFANG SUHONG CHEMICAL CO.,LTD
Contact:+86-838-2224563
Address:Room 1207 Zongchen Sunshine No.128 Taishan South Road,Deyang City,Sichuan China
Wuhan Better Organic Technology Inc.
Contact:13307163183
Address:Wuhan Economic&Technology Development Zone, Hubei
Jintan City Mego Chemical Co., Ltd
Contact:+86-0519-82814387
Address:23# Dengguan Town, Jintan, Jiangsu Province, China
Xi'an Kaixiang Photoelectric Technology Co., Ltd
website:http://www.kxmaterials.com/
Contact:86-29-15991651477
Address:Building 6, Biopharmaceutical Industry R&D Cluster Base, No. 16, Caotang 4th Road, Caotang Science and Technology Industrial Base, High-tech Zone, Xi'an City, Shaanxi Province, China
Contact:+86-28-88523492
Address:714rooms of Time Square, Pujiang County
Doi:10.1039/CT9099500878
(1909)Doi:10.1016/S0022-328X(00)87330-1
(1976)Doi:10.1016/j.tetlet.2020.152800
(2021)Doi:10.1016/S0040-4039(03)01615-0
(2003)Doi:10.1016/S0957-4166(03)00410-5
(2003)Doi:10.1016/S0277-5387(00)80757-3
(1989)