ChemicalBook CAS DataBase List 2,2,6,6-Tetramethyl-4-piperidinol

2,2,6,6-Tetramethyl-4-piperidinol synthesis

7synthesis methods

Product Name:2,2,6,6-Tetramethyl-4-piperidinol
CAS Number:2403-88-5
Molecular formula:C9H19NO
Molecular Weight:157.25

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2403-88-5
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Yield:2403-88-5 93%

Reaction Conditions:

with sodium tetrahydroborate in ethanol at 0 - 20; for 2 h;

Steps:

(2,2,6,6)-tetramethylpiperdin-4-ol
In a 500mL round bottom flask, 2,2,6,6-tetramethylpiperidin-4-one (15 g, 96.8 mmol) was diluted with 200 mL of absolute EtOH. The mixture was cooled to 0 °C and NaBH₄(1.5 equivalents, 5.5 g, 145 mmol) was carefully added portion wise (strong gas evolution). Reaction was allowed to reach room temperature under stirring for 2 hours and then cooled to 0 °C. Deionized water was slowly added (150 mL, white boron salt formation could be observed) and the mixture was warmed to room temperature overnight. After one extraction with AcOEt and concentration under vacuum the desired compound 1, was obtained as an orange solid (14.2 g, 93 %) and could be used without further purification. ¹H NMR 400 MHz CDCl₃ : δ 4.06 (m, 1H), 1.95 (dd, J=4.14 ; 12.47Hz, 2H), 1.33 (s, 1H), 1.24 (s, 6H), 1.11 (s, 6H), 1.0 (t, J=11.6Hz, 2H) ; ¹³C NMR 101 MHz CDCl₃ : δ 64.5, 51.66, 48.15, 34.91, 28.70.

References:

Membrat, Romain;Vasseur, Alexandre;Giordano, Laurent;Martinez, Alexandre;Nuel, Didier [Tetrahedron Letters,2019,vol. 60,# 3,p. 240 - 243] Location in patent:supporting information

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36768-62-4 Synthesis