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

HRID 1021064

반응식

HRID 1021064 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매2회

반응 조건

온도
-15 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1d5a8cc084d645c686ce643373bca8d2
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716495B2

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