ChemicalBook CAS DataBase List (S)-4-Benzyl-2-(2-hydroxyethyl)piperazine-1-carboxylic acid tert-butyl ester

(S)-4-Benzyl-2-(2-hydroxyethyl)piperazine-1-carboxylic acid tert-butyl ester synthesis

5synthesis methods

Product Name:(S)-4-Benzyl-2-(2-hydroxyethyl)piperazine-1-carboxylic acid tert-butyl ester
CAS Number:169447-92-1
Molecular formula:C18H28N2O3
Molecular Weight:320.43

24424-99-5 Synthesis

24424-99-5
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477220-33-0 Synthesis

(S)-4-(Phenylmethyl)-2-piperazineethanol

477220-33-0
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(S)-4-Benzyl-2-(2-hydroxyethyl)piperazine-1-carboxylic acid tert-butyl ester

169447-92-1
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Yield:169447-92-1 71%

Reaction Conditions:

in dichloromethane at 20; for 1 h;

Steps:

196

Combine (S)-2- (4-benzylpiperazin-2-yl) ethanol (3.08 g, 14.0 mmol) in methylenechloride (30 mL) and di-tert-butyl dicarbonate. (3.2 g, 14.7 mmol) in 5 mL CH2C12 and add dropwise at room temperature. After 1 hour, quench the reaction mixture by adding water, extract with CH2C12, wash with water and brine, and dry over Na2SO4. Purification by silica gel chromatography of the crude product by using MeOH/CH2Cl2 (5% to 10%) as the eluent, gives 3.17 g (Yield 71%) of title compound : IH NMR (400 MHz, CDC13) : 87. 37-7.23 (m, 5H), 4.27-4. 10 (m, 1H), 4.02-3. 80 (m, 2H), 3.61-3. 23 (m, 4H), 3.00 (t, 1H, J = 10 Hz), 2.71-2. 56 (m, 2H), 2.24-2. 22 (m, 2H), 2.01 (dt, 1H, J = 3.4, 12. 2 Hz), 1.46 (s, 9H).

References:

WO2003/82877,2003,A1 Location in patent:Page/Page column 97