Benzyl Bromide → (1R,2S,4R,5S)-5-(Benzyloxy)bicyclo[2.2.1]heptan-2-ol

HRID 46102

반응식

HRID 46102 반응식
[C@@H:1]12[CH2:8][C@@H:4]([C@@H:5]([OH:7])[CH2:6]1)[CH2:3][C@@H:2]2[OH:9].C1OCCOCCOCCOCCOC1.O1CCCC1.[OH-].[Na+].Br[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>>[CH2:33]([O:7][C@H:5]1[CH2:6][C@H:1]2[CH2:8][C@@H:4]1[CH2:3][C@@H:2]2[OH:9])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

참가 물질

6

반응물 5

HCID 7498Benzyl BromideHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 3633615-Crown-5HCID 9989289(1R,2S,4R,5S)-Bicyclo[2.2.1]heptane-2,5-diol

생성물 1

HCID 10036335(1R,2S,4R,5S)-5-(Benzyloxy)bicyclo[2.2.1]heptan-2-ol

반응 조건

온도
10 °C

실험 절차

To a stirred solution of (1R,2S,4R,5S)-bicyclo[2.2.1]-heptane-2,5-diol (1.15 g, 8.97 mmol) and 15-crown-5 (0.054 mL, 0.269 mmol) in tetrahydrofuran (30.0 mL, 8.97 mmol) were added at 10° C. (ice/water bath) finely ground sodium hydroxide (2.15 g, 53.8 mmol) and 1-(bromomethyl)benzene (1.07 mL, 8.97 mmol). After stirring at 10° C. for 3 h, the mixture was stirred at ambient temperature overnight. The mixture was partitioned between EtOAc and water, and the organic portions were washed with brine, and conc. in vacuo. The crude product was purified by flash column chromatography (0 to 80% of ethyl acetate in hexanes). The title compound was obtained as a colorless oil.

후처리

  1. stirringthe mixture was stirred at ambient temperature overnight
  2. customThe mixture was partitioned between EtOAc and water
  3. washthe organic portions were washed with brine
  4. customThe crude product was purified by flash column chromatography (0 to 80% of ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-0398e47c3d9a4f728465e8b40c186dab
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541592B2

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