Benzyl Bromide → HCID 70244349, 화합물

HRID 1068420노트

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HRID 1068420 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@@H:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=2)[C@H:10]([OH:21])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@@H:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=2)[C@H:10]([O:21][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 70204515HCID 70204515, 화합물

생성물 1

HCID 70244349HCID 70244349, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of trans-N-t-butoxycarbonyl-4-(3-methylphenyl)-3 hydroxy piperidine (131 mg, 0.449 mmol), in DMF (2 ml) at 0° C. was added sodium hydride (27 mg of a 60% dispersion in mineral oil, 0.890 mmol). After 10 min, benzyl bromide (0.107 ml, 0.890 mmol) was added and the reaction allowed to warm to room temperature over 16 hrs. The reaction was quenched by the addition of saturated NH4Cl solution (5 ml) and extraction with EtOAc. The organic extracts were washed with brine and dried (MgSO4) and the solvent evaporated in vacuo. Chromatography of the residue (SiO2, gradient elution, 10-15% EtOAc in hexanes) afforded the title compound as an oil.

후처리

  1. customThe reaction was quenched by the addition of saturated NH4Cl solution (5 ml) and extraction with EtOAc
  2. washThe organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. customthe solvent evaporated in vacuo
  5. washChromatography of the residue (SiO2, gradient elution, 10-15% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-29e9ac13a8284506ba30ba2f805b659c
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06248756B1

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