Sodium hydride → HCID 59371591, 화합물

HRID 2095449노트

반응식

HRID 2095449 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][OH:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[F:19][C:20]([F:30])([F:29])[C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][CH:22]=1.[NH4+].[Cl-]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][O:16][CH2:25][C:24]2[CH:23]=[CH:22][C:21]([C:20]([F:19])([F:29])[F:30])=[CH:28][CH:27]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 8541401-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidine

생성물 1

HCID 59371591HCID 59371591, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 1-(tert-butoxycarbonyl)-4-(2-hydroxyethyl)piperidine (302 mg, 1.32 mmol) in anhydrous THF (10 mL) was cooled to 0° C., and NaH (60% dispersion in oil, 63 mg, 1.58 mmol, 1.2 equiv.) was added all at once. Alkoxide formation was effected by stirring at room temperature for 2 h under N2, then 4-(trifluoromethyl)benzyl bromide (378 mg, 1.58 mmol, 1.2 equiv.) was added. The mixture was stirred at room temperature overnight. Saturated aqueous NH4Cl solution was added, and the product was extracted into EtOAc. The organic layer was dried over Na2SO4 and concentrated. The residue was purified by CC (SiO2, EtOAc/hexane 1:4) to afford the ether (496 mg, 97%) after evaporation. 1H NMR (CDCl3, 400 MHz) δ 7.59 (d, 2H, J=8.4 Hz), 7.43 (d, 2H, J=8.0 Hz), 4.54 (s, 2H), 4.06 (d, 2H, J=13.2 Hz), 5.31 (t, 2H, J=6.4 Hz), 2.68 (t, 2H, J=12.8 Hz), 1.58 (m, 5H), 0.89 (m, 2H).

후처리

  1. stirringThe mixture was stirred at room temperature overnight
  2. extractionthe product was extracted into EtOAc
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by CC (SiO2, EtOAc/hexane 1:4)
  6. customto afford the ether (496 mg, 97%)
  7. customafter evaporation

출처 및 근거

ORD 기록
ord-ea612b676532455e89f508be38d0ce61
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08445684B2

반응 노트

불러오는 중…