Hive Novel Discourse

	Main Index Search Register Login Who's Online FAQ Links
	Main Index Search Register Login Who's Online FAQ Links

	1 Online, 0 Active		You are not logged in

This is a historical archiveThe forum is read-only. Private information has been removed. It is not possible to login.

	Novel Discourse

All 3 posts Subject: Synthesis of (±)-erythro-Methylphenidate Please login to post Down

Rhodium
(Chief Bee)
07-10-03 11:37
No 446159
User Picture       Synthesis of (±)-erythro-Methylphenidate
(Rated as: excellent)

A Concise and Stereoselective Synthesis of (±)-erythro-Methylphenidate
Dennis Russowsky, and Brenno Amaro da Silveira Neto
Tetrahedron Letters, 44(14), 2923-2926 (2003) (https://www.rhodium.ws/pdf/erythro-methylphenidate.pdf)
DOI:10.1016/S0040-4039(03)00420-9

Abstract

A concise and stereoselective synthesis of racemic erythro-methylphenidate (1) is described. The coupling reaction between piperidine-2-thione (3) and 2-bromo-2- phenylmethylacetate (4) afforded the -enaminocarbonyl compound 2 in 60% yield by a modified Eschenmoser sulfide contraction reaction. In most cases the bicyclic thiazolidinone 5 was produced. Diastereoselective reduction of 2 in the presence of borohydrydes furnished the (±)-erythro-methylphenidate in good yields with dr >95%.

Rhodium
(Chief Bee)
06-03-04 16:40
No 511244
User Picture       Two Methylphenidate Syntheses
(Rated as: good read)

Über stereoisomere 2-Piperidylphenylessigsäure-methylester
I. Weisz & A. Dudás
Monatsheft für Chemie, 840-849 (1960) (https://www.rhodium.ws/pdf/methylphenidate.1960.pdf)
____ ___ __ _

Über die Darstellung von Pyridyl- und Piperidyl-aryl-acetonitrilen und einigen Umwandlungsprodukten. III Teil.
K. Scholz & L. Panizzon
Helv. Chim. Acta 37, 1605-1611 (1954) (https://www.rhodium.ws/pdf/methylphenidate.1954.pdf)

^{The Hive - Clandestine Chemists Without Borders}

cattleprodder
(Hive Bee)
06-04-04 21:32
No 511512
      2-benzylpiperidine

I wonder if benzyl bromide can be substituted for
Ph-CH(Br)CO2Me in the above synthesis to yield
2-benzylpiperidine.

	https://the-hive.archive.erowid.org	the-hive@erowid.org



Powered by Euphoria(TM) Release 4.00.5 early beta, © 2020 - 2022, Saint Nick Europe
Links Erowid Rhodium

	All 3 posts		Subject: Synthesis of (±)-erythro-Methylphenidate		Please login to post		Down


		Rhodium (Chief Bee) 07-10-03 11:37 No 446159				Synthesis of (±)-erythro-Methylphenidate (Rated as: excellent)
						*A Concise and Stereoselective Synthesis of (±)-erythro-Methylphenidate* Dennis Russowsky, and Brenno Amaro da Silveira Neto Tetrahedron Letters, 44(14), 2923-2926 (2003) (https://www.rhodium.ws/pdf/erythro-methylphenidate.pdf) DOI:10.1016/S0040-4039(03)00420-9 Abstract A concise and stereoselective synthesis of racemic erythro-methylphenidate (1) is described. The coupling reaction between piperidine-2-thione (3) and 2-bromo-2- phenylmethylacetate (4) afforded the -enaminocarbonyl compound 2 in 60% yield by a modified Eschenmoser sulfide contraction reaction. In most cases the bicyclic thiazolidinone 5 was produced. Diastereoselective reduction of 2 in the presence of borohydrydes furnished the (±)-erythro-methylphenidate in good yields with dr >95%.



		Rhodium (Chief Bee) 06-03-04 16:40 No 511244				Two Methylphenidate Syntheses (Rated as: good read)
						Über stereoisomere 2-Piperidylphenylessigsäure-methylester I. Weisz & A. Dudás Monatsheft für Chemie, 840-849 (1960) (https://www.rhodium.ws/pdf/methylphenidate.1960.pdf) ____ ___ __ _ Über die Darstellung von Pyridyl- und Piperidyl-aryl-acetonitrilen und einigen Umwandlungsprodukten. III Teil. K. Scholz & L. Panizzon Helv. Chim. Acta 37, 1605-1611 (1954) (https://www.rhodium.ws/pdf/methylphenidate.1954.pdf) ^{The Hive - Clandestine Chemists Without Borders}



		cattleprodder (Hive Bee) 06-04-04 21:32 No 511512				2-benzylpiperidine
						I wonder if benzyl bromide can be substituted for Ph-CH(Br)CO2Me in the above synthesis to yield 2-benzylpiperidine.

All 3 posts	End of thread	Top