Tert-butyl 3-benzoylpiperidine-1-carboxylate → Tert-butyl 3-(1-hydroxy-1-phenylheptyl)piperidine-1-carboxylate

HRID 1254188

반응식

HRID 1254188 반응식
[C:1]([CH:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:22]([Mg]Br)[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>C1COCC1>[OH:8][C:1]([CH:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

참가 물질

4

반응물 2

HCID 57449677Tert-butyl 3-benzoylpiperidine-1-carboxylateHCID 178444609HCID 178444609, 화합물

생성물 1

HCID 59382974Tert-butyl 3-(1-hydroxy-1-phenylheptyl)piperidine-1-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-10 °C

실험 절차

To a 100-mL round bottom flask were added tert-butyl 3-(benzoyl)piperidine-1-carboxylate (0.4733 g, 1.63 mmol, 1.0 equiv) and THF (5 mL). The flask was evacuated and refilled with N2. The mixture was cooled with a dry ice-acetone bath and hexylmagnesium bromide (2.0M solution in Et2O, 2.5 mL, 5.0 mmol, 3.0 equiv) was added. The reaction mixture was allowed to slowly warm to −10° C. while stirring overnight (17 h). The mixture was quenched with saturated NH4Cl (10 mL), extracted three times with EtOAc, and dried over Na2SO4. The crude product was purified by reversed-phase HPLC(XTerra® Prep MS C18 OBD™ Column, 5 μl, 19×50 mm, 10%→90% CH3CN/H2O, 0.1% CF3COOH over 8 min, flow rate 20 mL/min) to give tert-butyl 3-(1-hydroxy-1-phenylheptyl)piperidine-1-carboxylate. LC-MS (3 min) tR=2.41 min, m/z 398 (M+Na+), 376 (MH+), 302, 276, 258.

후처리

  1. customThe flask was evacuated
  2. additionrefilled with N2
  3. temperatureThe mixture was cooled with a dry ice-acetone bath
  4. customThe mixture was quenched with saturated NH4Cl (10 mL)
  5. extractionextracted three times with EtOAc
  6. dry with materialdried over Na2SO4
  7. customThe crude product was purified by reversed-phase HPLC(XTerra® Prep MS C18 OBD™ Column, 5 μl, 19×50 mm, 10%
  8. customover 8 min

출처 및 근거

ORD 기록
ord-f77450e355d84c85840777653ca5231b
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08455521B2

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