ChemicalBook CAS DataBase List D-alpha-Amino-epsilon-caprolactam

D-alpha-Amino-epsilon-caprolactam synthesis

8synthesis methods

Product Name:D-alpha-Amino-epsilon-caprolactam
CAS Number:28957-33-7
Molecular formula:C6H12N2O
Molecular Weight:128.17

7274-88-6 Synthesis

7274-88-6
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28957-33-7
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$45.00/50mg

Yield: 15%

Reaction Conditions:

with hexamethyldisilazan in toluene for 168 h;Heating / reflux;

Steps:

2.a
a) 3R-Amino-azepan-2-one D-Lysine hydrochloride (48 g, 0.26 mol) and hexamethyldisilazane (424.4 g, 2.6 mol) were suspended in toluene (1.1 litre) and refluxed for 1 week under an argon atmosphere, using a water-trap condenser. The reaction mixture was cooled to r.t. and slowly added to ice-cold MeOH (2.24 litre). The resultant clear solution was stirred for 30 min and concentrated under reduced pressure. The white, waxy solid was stirred in ethyl acetate, filtered and the filtrated concentrated under reduced pressure: white solid 5.4 g, (15%); ¹H NMR (CDCl₃) δ 1.35-2.05 (m, 8H), 3.2-3.26 (m, 2H), 3.53 (dd, 1H), 6.10 (br, 1H) MS: m/e=129.2 (MH⁺)

References:

Galley, Guido;Kitas, Eric Argirios;Jakob-Roetne, Roland US2006/14945, 2006, A1 Location in patent:Page/Page column 41