Dichloromethane → 3-({[(2R,3R,7S)-2,3-diphenyl-1,4-dioxaspiro[4.5]dec-7-yl]methyl}amino)-4-nitrobenzonitrile

HRID 715493

반응식

HRID 715493 반응식
F[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[C:5]#[N:6].[C:13]1([C@@H:19]2[C@@H:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:22][C:21]3([CH2:34][CH2:33][CH2:32][C@H:31]([CH2:35][NH2:36])[CH2:30]3)[O:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>C(#N)C.CO>[C:13]1([C@@H:19]2[C@@H:23]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[O:22][C:21]3([CH2:34][CH2:33][CH2:32][C@H:31]([CH2:35][NH:36][C:2]4[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=4[N+:10]([O-:12])=[O:11])[C:5]#[N:6])[CH2:30]3)[O:20]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 27833993-Fluoro-4-nitrobenzonitrileHCID 711160531-[(2R,3R,7S)-2,3-diphenyl-1,4-dioxaspiro[4.5]dec-7-yl]methanamine

생성물 1

HCID 711162093-({[(2R,3R,7S)-2,3-diphenyl-1,4-dioxaspiro[4.5]dec-7-yl]methyl}amino)-4-nitrobenzonitrile수율 88%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6342Acetonitrile용매

실험 절차

A mixture of 3-fluoro-4-nitrobenzonitrile (55.5 g, 334 mmol), 1-[(2R,3R,7S)-2,3-diphenyl-1,4-dioxaspiro[4.5]dec-7-yl]methanamine (103 g, 318 mmol) and potassium carbonate (88 g, 637 mmol) in acetonitrile (2654 mL) was stirred at RT for 5 days (˜200 mL DCM was added to help with solubility). The resulting solution was filtered and the solids washed with MeCN. The resulting solution was concentrated to give the crude product that was dissolved in MeOH (500 mL) and allowed to crystallize with stirring. The slurry was allowed to stir at RT overnight, filtered and the solids dried under reduced pressure to give 3-({[(2R,3R,7S)-2,3-diphenyl-1,4-dioxaspiro[4.5]dec-7-yl]methyl}amino)-4-nitrobenzonitrile (131.41 g, 88% yield). The product was used without further purification.

후처리

  1. filtrationThe resulting solution was filtered
  2. washthe solids washed with MeCN
  3. concentrationThe resulting solution was concentrated
  4. customto give the crude product that
  5. customto crystallize
  6. stirringwith stirring
  7. stirringto stir at RT overnight
  8. filtrationfiltered
  9. customthe solids dried under reduced pressure

출처 및 근거

ORD 기록
ord-487b7f2e91fd435589bbee19d4572d21
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187464B2

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