반응 #89770

반응 방정식

(1S,2S,5S)-5-benzyl-2-[(4-phenylpiperazin-1-yl)carbonyl]-6-oxabicyclo[3.2.1]-octan-7-one

hydroxylamine

→

product

수율 26.0%

(1S,2S,5S)-5-benzyl-N,5-dihydroxy-2-[(4-phenylpiperazin-1-yl)carbonyl]-cyclohexanecarboxamide

수율 26.0%

용매

methanol

methanol

반응 조건

후처리

1. 1
   기타The reaction was quenched with saturated aqueous NH4Cl (15 mL)
2. 2
   추출extracted with EtOAc (2×)
3. 3
   세척The combined organic layers were washed with brine
4. 4
   건조dried over sodium sulfate
5. 5
   여과filtered
6. 6
   농축concentrated in vacuo
7. 7
   기타The residue was purified by reverse phase HPLC with 5-95% MeCN/H2O (with 0.05% TFA)

실험 절차

To a stirred solution of (1S,2S,5S)-5-benzyl-2-[(4-phenylpiperazin-1-yl)carbonyl]-6-oxabicyclo[3.2.1]-octan-7-one (8.0 mg, 0.020 mmol) in anhydrous methanol (1.0 mL, 0.025 mol) at rt was added 1.50 M of hydroxylamine in methanol (0.396 mL). The reaction mixture was stirred at rt for 3 h. The reaction was quenched with saturated aqueous NH4Cl (15 mL), extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by reverse phase HPLC with 5-95% MeCN/H2O (with 0.05% TFA) to give the pure product as a colorless solid (2.3 mg, 26% in yield). MS (ESI): (M+H)+=438.1.

출처