Sodium hydride → 4-(oxiran-2-ylmethoxy)-1H-indole

HRID 40629

반응식

HRID 40629 반응식
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[H-].[Na+].[N+](C1C=C(S(O[CH2:26][C@@H:27]2[O:29][CH2:28]2)(=O)=O)C=CC=1)([O-])=O>CN(C)C=O.C(OCC)(=O)C.CCCCCCC>[O:29]1[CH2:28][CH:27]1[CH2:26][O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2

참가 물질

7

반응물 3

HCID 24758Sodium hydrideHCID 754211H-indol-4-olHCID 146513Benzenesulfonic acid, 3-nitro-, (2R)-2-oxiranylmethyl ester

생성물 1

HCID 6050154-(oxiran-2-ylmethoxy)-1H-indole

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매3회HCID 8900Heptane용매

실험 절차

4-hydroxy indole (0.08 g, mmol) was dissolved in dimethylformamide (1.5 mL). Sodium hydride (0.02 g, 0.51 mmol) was slowly added to the reaction mixture followed by addition of (R)-glycidyl 3-nitrobenzene sulfonate (0.132, 0.51 mmol). A red color appeared. After 3 hour the reaction mixture was poured into a separatory funnel and ethyl acetate (100 mL) was added. The organic layer was washed 3 times with a 10% solution of sodium carbonate in water. The aqueous layers were discarded, the organic layer was dried with sodium sulfate and the solvent was removed by reduced pressure to yield crude product. The crude product was dissolved in ethyl acetate, Celite® (approximately 3 grams) was added, followed by removal of the solvent under reduced pressure. The Celite®/reaction mixture was loaded into an Isco solid phase loading cartridge. Flash chromatography was carried out using an Isco Companion automated chromatography system, silica column (4 g), initially holding at 5% ethyl acetate in heptane for 3 column volumes, increasing the ethyl acetate concentration to 60% over 40 column volumes, holding at 60% ethyl acetate for 10 more column volumes to yield the title compound as a residue.

후처리

  1. additionAfter 3 hour the reaction mixture was poured into a separatory funnel
  2. washThe organic layer was washed 3 times with a 10% solution of sodium carbonate in water
  3. dry with materialthe organic layer was dried with sodium sulfate
  4. customthe solvent was removed by reduced pressure
  5. customto yield crude product
  6. additionCelite® (approximately 3 grams) was added
  7. customfollowed by removal of the solvent under reduced pressure
  8. customThe Celite®/reaction mixture
  9. temperatureincreasing
  10. concentrationthe ethyl acetate concentration to 60% over 40 column volumes

출처 및 근거

ORD 기록
ord-84fa0ae3d8e145d5992da9e839ad5898
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530475B2

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