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ChemicalBook CAS DataBase List 2-AMINO-2-BUTYLHEXANOL

2-AMINO-2-BUTYLHEXANOL synthesis

3synthesis methods
Norleucine, 2-butyl-, ethyl ester

393855-78-2
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2-AMINO-2-BUTYLHEXANOL

288161-81-9
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Yield:288161-81-9 95%

Reaction Conditions:

Stage #1: 2-amino-2-butyl-hexanoic acid ethyl esterwith lithium aluminium tetrahydride in tetrahydrofuran at 20 - 65;
Stage #2: with sodium hydroxide in tetrahydrofuran;water at 0; for 2 h;

Steps:

5

A solution of ethyl 2-butylnorleucinate (37 g, 172 mmol) in THF (275 mL) at 25 °C was treated with 2M LAH (86 mL, 172 mmol) via an addition funnel over 30 min. The reaction mixture was heated to 65°C and stirred for 2 h then allowed to come to ambient temperature while stirring overnight. The reaction was cooled to 0°C then treated sequentially with H20 (7.82 mL), 15% NaOH (7.82 mL), and H2O (23.5 mL). The mixture was stirred for 2 h then filtered washing with THF. The filtrate was concentrated in vacuo to give 2-amino-2-butyl-1 -hexanol (29.8 g, >95% yield) as a thick yellow oil which solidified upon standing.

References:

WO2011/137135,2011,A1 Location in patent:Page/Page column 44