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ChemicalBook CAS DataBase List (S)-DI-TERT-BUTYL 2-(HYDROXYMETHYL)PIPERAZINE-1,4-DICARBOXYLATE
958635-12-6

(S)-DI-TERT-BUTYL 2-(HYDROXYMETHYL)PIPERAZINE-1,4-DICARBOXYLATE synthesis

4synthesis methods
-

Yield:958635-12-6 100%

Reaction Conditions:

Stage #1: (2S)-1,4-bis(tert-butoxycarbonyl)piperazine-2-carboxylic acidwith borane in tetrahydrofuran at 20; for 4 h;Heating / reflux;
Stage #2: with methanol in tetrahydrofuran at 0;

Steps:

3

(S)-2-Piperazine- 1,2,4-tricarboxylic acid 1 ,4-di-te/t-butyl ester (9.90 g, 30.0 mmol) was dissolved in THF (14 mL). IM borane in THF (90 mL, 90.0 mmol) was added at room temperature. The reaction mixture was stirred at reflux for 4 hours and then cooled to 0 0C and quenched with the drop-wise addition of methanol (100 mL) and then concentrated in vacuo to give (S)-2-hydroxymethyl-piperazine-l,4-dicarboxylic acid di-tert-buty{ ester (12.07 g, 127%) as a white solid which was used without further purification. Analytical LCMS: purity 100% (System C, Rτ = 2.08 min), ES+: 339.4 [MH]+.

References:

WO2009/71658,2009,A1 Location in patent:Page/Page column 26