Cesium carbonate → (R)-2'-bromo-7'-(neopentyloxy)spiro[morpholine-3,9'-xanthen]-5-one

HRID 455721노트

반응식

HRID 455721 반응식
[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8]([OH:16])=[CH:9][CH:10]=3)[C:5]3([CH2:21][O:20][CH2:19][C:18](=[O:22])[NH:17]3)[C:4]=2[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:30][C:31]([CH3:34])([CH3:33])[CH3:32]>CN(C=O)C>[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8]([O:16][CH2:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:9][CH:10]=3)[C@:5]3([CH2:21][O:20][CH2:19][C:18](=[O:22])[NH:17]3)[C:4]=2[CH:3]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 84953Propane, 1-iodo-2,2-dimethyl-HCID 674375182'-Bromo-7'-hydroxyspiro[morpholine-3,9'-xanthen]-5-one

생성물 1

HCID 67437748(R)-2'-bromo-7'-(neopentyloxy)spiro[morpholine-3,9'-xanthen]-5-one

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
115 °C

실험 절차

In a 25-ml flask, 2′-bromo-7′-hydroxyspiro[morpholine-3,9′-xanthen]-5-one (0.020 g, 0.055 mmol) was dissolved in DMF (1 mL). Cesium carbonate (0.043 g, 0.133 mmol) was added, followed by 1-iodo-2,2-dimethylpropane (0.022 g, 0.110 mmol). The reaction was heated in a 115° C. oil bath for 10 h. The reaction was cooled to ambient temperature and concentrated. The residue was taken up in 0.3 M aqueous HCl (15 mL) and the aqueous layer was extracted with EtOAc (3×20 mL). The organic layers were combined, washed with saturated brine (5 mL), dried over sodium sulfate, and concentrated. The residue was purified by chromatography (25% EtOAc/hexane) to afford (R)-2′-bromo-7′-(neopentyloxy)spiro[morpholine-3,9′-xanthen]-5-one.

후처리

  1. temperatureThe reaction was cooled to ambient temperature
  2. concentrationconcentrated
  3. extractionthe aqueous layer was extracted with EtOAc (3×20 mL)
  4. washwashed with saturated brine (5 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography (25% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-1551e13cda0b438e86f97c60dae61ad3
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497264B2

반응 노트

불러오는 중…