ChemicalBook CAS DataBase List (2S,5S)-5-hydroxypiperidine-2-carboxylic acid hydrochloride

(2S,5S)-5-hydroxypiperidine-2-carboxylic acid hydrochloride synthesis

8synthesis methods

Product Name:(2S,5S)-5-hydroxypiperidine-2-carboxylic acid hydrochloride
CAS Number:154307-84-3
Molecular formula:C6H12ClNO3
Molecular Weight:181.62

(2S,5S)-tert-butyl 5-hydroxypiperidine-2-carboxylate(2S,5S)-tert-butyl 5-hydroxypiperidine-2-carboxylate

1383814-52-5
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(2S,5S)-5-hydroxypiperidine-2-carboxylic acid hydrochloride

154307-84-3
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$35.00/100mg

Yield:154307-84-3 96%

Reaction Conditions:

with hydrogenchloride in water at 20 - 65; for 2 h;

Steps:

114.1 Step 1 Hydrochloride of (2S,5S)-5-hydroxypiperidine-2-carboxylic acid (7)

Step 1 Hydrochloride of (2S,5S)-5-hydroxypiperidine-2-carboxylic acid (7) [0646] (2S,5S)-tert-Butyl 5-hydroxypiperidine-2-carboxylate (126.22g, 0.63 mol) described in Example 1 was gradually added into 5M hydrochloric acid (630 mL) at room temperature, followed by heating to 65 °C and stirring for 2 hours. Subsequently, the reaction solution was cooled to room temperature and the reaction solvent was concentrated under reduced pressure. The residue was dissolved in water (500 mL), and activated carbon (6.5 g) was added, followed by stirring at room temperature for 30 minutes. The activated carbon was filtered through Celite. Celite was washed twice with water (100 mL) and the filtrate was combined, followed by concentrating under reduced pressure. The residue (150 g) was ice-cooled, followed by inoculation and stirring. To the mixture was added dropwise acetone (650 mL) over 30 minutes, followed by stirring for 30 minutes. The deposited crystals were filtered off under an argon stream, followed by washing with acetone. After deliquoring and drying under vacuum overnight, 108.79 g of the title compound was afforded as a colorless powder crystal (yield 96%). ¹H NMR (400 MHz, D₂O) δ 1.66-2.23 (m, 4H), 3.25 (d, J = 3.4 Hz, 1H), 3.38 (d, J = 3.4 Hz, 1H), 4.00 (dd, J = 11.7, 3.7 Hz, 1H), 4.22 (brs, 1H); MS m/z: 146 (M-HCl+H)⁺.

References:

EP2857401,2015,A1 Location in patent:Paragraph 0646

1253856-42-6 Synthesis