Water → (R)-5-Biphenyl-4-ylmethyl-1-(2,2-dimethylpropionyl)-1,5-dihydropyrrol-2-one

HRID 1021064

反応式

HRID 1021064 の反応式
[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][C:4]([CH2:7][C@H:8]2[N:12]([C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])[C:11](=[O:19])[CH2:10][CH2:9]2)=[CH:3][CH:2]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C1([Se]Br)C=CC=CC=1.O>C1(C)C=CC=CC=1>[C:1]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:2]=[CH:3][C:4]([CH2:7][C@H:8]2[N:12]([C:13](=[O:18])[C:14]([CH3:16])([CH3:17])[CH3:15])[C:11](=[O:19])[CH:10]=[CH:9]2)=[CH:5][CH:6]=1

参加物

6

反応物 4

HCID 962WaterHCID 123446BromoselenobenzeneHCID 2733832Lithium HexamethyldisilazideHCID 58160363(S)-5-[(biphenyl-4-yl)methyl]-1-(2,2-dimethylpropionyl)pyrrolidin-2-one

生成物 1

HCID 59318479(R)-5-Biphenyl-4-ylmethyl-1-(2,2-dimethylpropionyl)-1,5-dihydropyrrol-2-one

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

反応条件

温度
-15 °C

実験手順

1.68 g (S)-5-biphenyl-4-ylmethyl-1-(2,2-dimethylpropionyl)pyrrolidin-2-one (1, R1=pivaloyl) is added to 10 ml toluene. The mixture is then cooled to −15° C. 5.5 ml Lithium bis(trimethylsilyl)amide (1 M in THF) is then added. After 1 h, a mixture of 1.3 g phenyl selenyl bromide in 10 ml toluene is added. After a further 30 min, 100 ml water is added. The phases are separated and the organic phase concentrated in vacuo. The residue is taken up in 25 ml ethyl acetate and then 5.1 ml hydrogen peroxide (37%) is added at room temperature. After 1 h, the phases are separated and the organic phase washed with a saturated sodium hydrogen carbonate solution and then dried (MgSO4). The mixture is concentrated in vacuo and purified by column chromatography, eluting with heptane/ethyl acetate 5:1 to afford (R)-5-Biphenyl-4-ylmethyl-1-(2,2-dimethylpropionyl)-1,5-dihydropyrrol-2-one. 1H NMR (CDCl3): 1.28 (9H), 2.70 (1H), 3.30 (1H), 4.97 (1H), 5.89 (1H), 7.06 (2H), 7.19 (2H), 7.31 (2H), 7.41 (4H).

後処理

  1. additionis added
  2. waitAfter a further 30 min
  3. customThe phases are separated
  4. concentrationthe organic phase concentrated in vacuo
  5. addition5.1 ml hydrogen peroxide (37%) is added at room temperature
  6. waitAfter 1 h
  7. customthe phases are separated
  8. washthe organic phase washed with a saturated sodium hydrogen carbonate solution
  9. dry with materialdried (MgSO4)
  10. concentrationThe mixture is concentrated in vacuo
  11. custompurified by column chromatography
  12. washeluting with heptane/ethyl acetate 5:1

出典と根拠

ORDレコード
ord-1d5a8cc084d645c686ce643373bca8d2
出典データセット
uspto-grants-2014_05
特許番号
US08716495B2

関連ノート

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