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Synlett 2011(13): 1920-1922  
DOI: 10.1055/s-0030-1260951
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

N-Formylsaccharin: A New Formylating Agent

Thomas Cocheta, Véronique Bellostaa, Alfred Greinerb, Didier Rocheb, Janine Cossy*a
a Laboratoire de Chimie Organique, ESPCI ParisTech, CNRS, 10 Rue Vauquelin, 75231 Paris Cedex 05, France
Fax: +33(1)40794660; e-Mail: janine.cossy@espci.fr;
b Edelris s.a.s., 115 Avenue Lacassagne, 69003 Lyon, France
Further Information

Publication History

Received 15 April 2011
Publication Date:
14 July 2011 (online)

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Abstract

N-Formylsaccharin, a very cheap reagent, has been revealed to be an efficient and chemoselective formylating agent of amines.

Key words

formylation - amine - amino alcohol - saccharin

    References and Notes

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29

Typical Procedure for Amines To a suspension of N-formylsaccharin (211 mg, 1 mmol, 1 equiv) in anhyd THF (1 mL) at r.t., the requisite primary or secondary amine was added (1 mmol, 1 equiv). After 15 min at r.t., the reaction mixture was diluted with CH2Cl2 (10 mL), and a sat. aq NaHCO3 solution (10 mL) was added, the layers were separated, and the aqueous layer extracted with CH2Cl2 (2 × 10 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to afford pure
N-formylated amines.

30

Typical Procedure for Amino Alcohols To a suspension of N-formylsaccharin (211 mg, 1 mmol,
1 equiv) in anhyd THF (1 mL) at r.t., the requisite amino alcohol was added (1 mmol, 1 equiv). After 15 min at r.t., the reaction mixture was diluted with CH2Cl2 (5 mL), (piperidinomethyl)polystyrene (loading: 4 mmol/g, 750 mg) was added, and the reaction mixture was stirred at r.t. After 10 min, the reaction mixture was filtered through Celite® and concentrated in vacuo to afford pure N-formylated amino alcohols.