ChemicalBook CAS DataBase List N-Boc-piperidine-2-methanol

N-Boc-piperidine-2-methanol synthesis

7synthesis methods

Product Name:N-Boc-piperidine-2-methanol
CAS Number:157634-00-9
Molecular formula:C11H21NO3
Molecular Weight:215.29

24424-99-5

3433-37-2

157634-00-9

The general procedure for the synthesis of 1-Boc-2-piperidinemethanol from di-tert-butyl dicarbonate and 2-piperidinemethanol is as follows: 1. 2-Piperidinemethanol (3.0 g, 25.60 mmol) was dissolved in dichloromethane (DCM, 100 mL) under stirring. 2. triethylamine (14.5 mL, 91.08 mmol) was added to the above solution in batches, followed by di-tert-butyl dicarbonate (7.2 g, 31.0 mmol). 3. The reaction mixture was stirred at room temperature for 16 hours. 4. Upon completion of the reaction, water (70 mL) was added for stratification to separate the organic layer. 5. The organic layer was washed with water (2 x 50 mL) and then dried with anhydrous sodium sulfate (Na2SO4). 6. The dried organic layer was filtered and concentrated under vacuum to give 1-Boc-2-piperidinemethanol (6.0 g, quantitatively) as a light brown oil, which can be used without further purification. The nuclear magnetic resonance hydrogen spectrum (1H NMR, CDCl3) data were as follows: δ 4.42-4.22 (1H, m), 4.05-3.91 (1H, m), 3.89-3.77 (1H, m), 3.71-3.53 (1H, m), 2.97-2.81 (1H, m), 2.32-2.08 (1H, m), 1.90 (1H, s ), 1.77-1.57 (3H, m), 1.54 (1H, s), 1.52-1.38 (10H, m).

24424-99-5 Synthesis

24424-99-5
861 suppliers
$13.50/25G

3433-37-2 Synthesis

3433-37-2
245 suppliers
$7.00/5g

157634-00-9
204 suppliers
$5.00/1g

Yield:157634-00-9 100%

Reaction Conditions:

with triethylamine in dichloromethane at 20; for 16 h;

Steps:

INTERMEDIATE 28 (METHOD Z); ferf-Butyl 2-(hydroxymethyl^*)piperidine- 1 -carboxylate; To a stirred solution of 2-piperidinemethanol (3.0 g, 25.60 mmol) in DCM (100 mL) was added triethylamine (14.5 mL, 91.08 mmol) and then di-tert-butyl dicarbonate (7.2 g, 31.0 mmol) portionwise. The reaction mixture was stirred at r.t. for 16 h. Water (70 mL) was added and the layers were separated. The organic layer was washed with water (2 x 50 mL), dried (Na₂SO₄), filtered and concentrated in vacuo to give the title compound (6.0 g, quantitative) as a pale brown oil that was used without further purification. δ_H (CDCl₃) 4.42-4.22 (IH, m), 4.05-3.91 (IH, m), 3.89-3.77 (IH, m), 3.71- 3.53 (IH, m), 2.97-2.81 (IH, m), 2.32-2.08 (IH, m), 1.90 (IH, s), 1.77-1.57 (3H, m), 1.54 (IH, s), 1.52-1.38 (1OH, m).

References:

WO2007/141504,2007,A1 Location in patent:Page/Page column 57

98303-20-9 Synthesis