Solid phase parallel synthesis of tertiary amines

Details Solid phase parallel synthesis of tertiary amines Solid phase parallel synthesis of tertiary amines

2005-10-04

2005-10-04

Barts, Samuel (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

C564S391000, C564S462000

Reexamination Certificate

active

06951958

ABSTRACT:
Described is method for preparing tertiary amines comprising sequential, exhaustive alkylation of a hydroxylamine derivative and cleavage of the O—N bond using the following steps:a) reacting the hydroxylamine derivative with an alkylating agent or with a carbonyl compound to form an oxime intermediate.b) reacting the oxime intermediate with a reducing agent to produce an alkylated derivativec) reacting the alkylated derivative with an alkylating agent or a carbonyl compound in the presence of a reducing agent to produce a dialkylated derivatived) reacting the dialkylated derivative with an alkylating agent to produce a quaternized derivativee) reacting the quaternized derivative with a reagent causing cleavage of the O—N bond to produce a tertiary amine.

REFERENCES:
patent: 6133409 (2000-10-01), Salvino et al.
patent: WO 98/29376 (1998-07-01), None
patent: WO 99/09073 (1999-02-01), None
Joseph M. Salvino, et al.: “Parallel Synthesis of Aldehydes and Ketone Facilitated by a New Solid-Phase Weinreb Amide”, Journal of Organic Chemistry, vol. 64, No. 6, Mar. 19, 1999, pp. 1823-1830, XP002152402, American Chemical Society, Easton, US ISSN: 0022-3263 cited in the application p. 1824, col. 1, line 1—p. 1937, col. 2, line 26.
Angelo Liguori, et al.: “Novel Approach to the Ring-Opening Reaction of Isoxazolidinium Salts to 1,3-Amino Alcohols”, Chemische Berichte, vol. 121, 1988, pp. 105-109, XP002152403, Weinheim, DE.; cited in the application p. 105, col. 1, line 1—p. 106, col. 2, line 18.
Eric E. Swayze, et al.: “The Synthesis of N, N'-O-Trisubstituted Hydroxylamines via a Mild Reductive Alkylation Procedure: An Improved Synthesis of the MMI Backbone”; Synlett, No. 7, Jul. 1997, paged 859-861, XP002152404, Thieme Verlag, Stuttgart, DE., ISSN: 0936-5214 cited in the application the whole document.

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