(S)-benzyl 3-(hydroxymethyl)piperazine-1-carboxylate synthesis

Yield:-

Reaction Conditions:

in ISOPROPYLAMIDE;water;acetonitrile at 0 - 20; for 0.25 h;

Steps:

1.C
Step C: To a solution of compound 1B (207 mg, 1.78 mmol) in CH₃CN/DMA/H₂O (1 mL, 0.3 mL, 0.7 mL) cooled to 0° C. was added dropwise CBZ-OSu (444 mg, 1.78 mmol) in DMA (0.5 mL). The reaction was stirred for 15 min at 0° C. then slowly warmed to RT. To the reaction was added H₂O (30 mL) and sat'd NaHCO₃ (5 mL), and then the product was extracted three times with EtOAc (20 mL). The combined EtOAc layers were washed twice with brine, dried over MgSO₄ then concentrated in vacuo to give crude (S)-benzyl 3-(hydroxymethyl)piperazine-1-carboxylate (256 mg). HPLC RT: 1.082 min (4 min Chromolith column TFA). (M+H)⁺:251

References:

Bristol-Myers Squibb Company US2007/88039, 2007, A1 Location in patent:Page/Page column 19

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