Efficient synthesis of primary 2-aminothiols from 2-aminoalcohols and methyldithioacetate

Tetrahedron Letters

Volumn 49, Issue 46, 2008, Pages 6553-6555

  Mercey, Guillaume ^a   Brégeon, Delphine ^a   Gaumont, Annie Claude ^a   Levillain, Jocelyne ^a   Gulea, Mihaela ^a  

^a UNIVERSITÉ DE CAEN   (France)

Author keywords

Aminoalcohol; Aminothiol; Dithioester; Thiazoline; Thioamide

Indexed keywords

ACETIC ACID DERIVATIVE; ALCOHOL DERIVATIVE; SULFUR; THIOL DERIVATIVE;

ACYLATION; AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DEPROTECTION REACTION; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 52949090004     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.09.014     Document Type: Article

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38. 2O (15 mL) was added to precipitate the triethyl ammonium salt. After filtration, solvents were evaporated and the residual oil was purified by flash chromatography on silica gel affording thiazoline 3.(iii) Hydrolysis: Thiazoline 3 (2 mmol) was placed in a degazed aqueous solution of HCl 5 N (10 mL), under nitrogen atmosphere. The mixture was heated under reflux for 24-192 h. After cooling to room temperature, the aqueous layer was washed with ether (3 × 5 mL), then with dichloromethane (3 × 5 mL). After removal of the water under vacuum, the residue was triturated with acetone, filtered, and dried to give the corresponding aminothiol hydrochloride 4.