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

HRID 1900050ノート

反応式

HRID 1900050 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 10865532Bis(triphenylphosphine)palladium(II) diacetate触媒HCID 284Formic Acid溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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°.

後処理

  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

出典と根拠

ORDレコード
ord-edeac957a11f46438998f5309f817f20
出典データセット
uspto-grants-1996_11
特許番号
US05574055

反応ノート

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