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ChemicalBook CAS DataBase List 2-(1-(Tert-Butoxycarbonyl)-4-Hydroxypiperidin-4-Yl)Acetic Acid

2-(1-(Tert-Butoxycarbonyl)-4-Hydroxypiperidin-4-Yl)Acetic Acid synthesis

4synthesis methods
-

Yield:502482-52-2 100%

Reaction Conditions:

Stage #1: 4-ethoxycarbonylmethyl-4-hydroxypiperidine-1-carboxylic acid tert-butyl esterwith water;sodium hydroxide in methanol; for 3 h;Reflux;
Stage #2: with hydrogenchloride in water; pH=4;

Steps:

12

00165] The material (730 mg) from the previous step was dissolved in the mixture of methanol (5 mL) and NaOH solution (10 N, 1 mL). The resulting mixture was refluxed for 3 hours and then cooled to room temperature. The solvent was evaporated, and the residue was re-dissolved in water and then extracted with diethyl ether. The aqueous solution was neutralized with cone. HC1 until pH = 4, and the aqueous layer was then extracted with dichloromethane. The combineddichloromethane layers were dried over NaS04. Evaporation of solvent gave 32 as white solid. 1H NMR (300 mHz ;CDC13) δ 1.44 (s, 9 H), 1.48 (m, 2 H), 1.66 (d, 2 H, J= 12.99 Hz), 2.46 (s, 2 H), 3.13 (t, 2 H, J = 11.7 Hz), 3.76 (b, 2 H).

References:

WO2011/32291,2011,A1 Location in patent:Page/Page column 52