Sodium hydride → (S)-(+)-4-(2,3-Epoxypropoxy)carbazole

HRID 40631

반응식

HRID 40631 반응식
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[C:4]([OH:14])=[CH:3][CH:2]=1.[H-].[Na+].[N+](C1C=C(S(O[CH2:30][C@H:31]2[O:33][CH2:32]2)(=O)=O)C=CC=1)([O-])=O>CN(C=O)C>[O:33]1[CH2:32][C@H:31]1[CH2:30][O:14][C:4]1[C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[NH:12][C:13]=2[CH:1]=[CH:2][CH:3]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 1042514-HydroxycarbazoleHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl ester

생성물 1

HCID 10879208(S)-(+)-4-(2,3-Epoxypropoxy)carbazole

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

9H-Carbazol-4-ol (0.367 g, 2.0 mmol) was placed in a flask with DMF (10 mL) and NaH (60% dispersion in oil, 77 mg, 2.0 mmol) and stirred for 30 min at room temperature. (S)-glycidyl 3-nitrobenzene sulfonate (0.52 g, 2.0 mmol) was added to the reaction mixture, which was then stirred at room temperature for 14 hours. The reaction was quenched with NaHCO3 (saturated) and then extracted with ethyl acetate (3×). The organic layer was dried with magnesium sulfate, filtered and the solvent evaporated under reduced pressure to yield crude product which was purified by silica gel chromatography (60% Ethyl acetate/heptane) to yield the title compound as a residue.

후처리

  1. stirringwas then stirred at room temperature for 14 hours
  2. customThe reaction was quenched with NaHCO3 (saturated)
  3. extractionextracted with ethyl acetate (3×)
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent evaporated under reduced pressure
  7. customto yield crude product which
  8. customwas purified by silica gel chromatography (60% Ethyl acetate/heptane)

출처 및 근거

ORD 기록
ord-e8c5a1c36f5d4ec695ceb777a2da6bf8
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530475B2

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