Dimethylformamide → 3-[(1RS,2RS,4SR)-4-Bicyclo[2.2.1]-hept-2-yl-phenyl]-5-methoxymethyl-oxazolidin-2-one

HRID 1900050노트

반응식

HRID 1900050 반응식
I[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH:11]([CH2:13][O:14][CH3:15])[O:10][C:9]2=[O:16])=[CH:4][CH:3]=1.[CH:17]12[CH2:23][CH:20]([CH2:21][CH2:22]1)[CH:19]=[CH:18]2.N1CCCCC1.CN(C)C=O>C(OCC)(=O)C.CC(O)=O.CC(O)=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd].C(O)=O>[CH:17]12[CH2:23][CH:20]([CH2:21][CH2:22]1)[CH2:19][CH:18]2[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH:11]([CH2:13][O:14][CH3:15])[O:10][C:9]2=[O:16])=[CH:4][CH:3]=1

참가 물질

8

반응물 4

HCID 6228DimethylformamideHCID 8082PiperidineHCID 103522-NorborneneHCID 22636831(RS)-3-(4-iodophenyl)-5-methoxymethyl-oxazolidin-2-one

생성물 1

HCID 700506373-[(1RS,2RS,4SR)-4-Bicyclo[2.2.1]-hept-2-yl-phenyl]-5-methoxymethyl-oxazolidin-2-one

시약·촉매·용매 3

HCID 10865532Bis(triphenylphosphine)palladium(II) diacetate촉매HCID 284Formic Acid용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 56 mg of bis-(triphenylphosphine)-palladium (II) diacetate, 0.5 g of (RS)-3-(4-iodophenyl)-5-methoxymethyl-oxazolidin-2-one, 0.16 g of bicyclo[2.2.1]hept-2-ene, 0.5 ml of piperidine, 1 ml of dimethylformamide and 0.15 ml of formic acid was stirred for 3 hours under an argon atmosphere. The reaction mixture was diluted with 50 ml of ethyl acetate and the separated precipitate was removed. The filtrate was extracted twice with 20 ml of water each time, the organic phase was dried over magnesium sulfate and the solvent was distilled off. The brown oil obtained was chromatographed on a 30-fold amount of silica gel with ethyl acetate/hexane (7:3), with 0.43 g of uniform product being obtained after crystallization in ethyl acetate/hexane while cooling. The racemic (1:1) diastereomer mixture melted at 83°-84°.

후처리

  1. customthe separated precipitate was removed
  2. extractionThe filtrate was extracted twice with 20 ml of water each time
  3. dry with materialthe organic phase was dried over magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customThe brown oil obtained
  6. customwas chromatographed on a 30-fold amount of silica gel with ethyl acetate/hexane (7:3), with 0.43 g of uniform product
  7. custombeing obtained
  8. customafter crystallization in ethyl acetate/hexane
  9. temperaturewhile cooling

출처 및 근거

ORD 기록
ord-edeac957a11f46438998f5309f817f20
출처 데이터셋
uspto-grants-1996_11
특허 번호
US05574055

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