2,2,6,6-Tetramethylpiperidine → HCID 68814650, 화합물

HRID 732343

반응식

HRID 732343 반응식
C([Li])CCC.CC1(C)CCCC(C)(C)N1.[C:16]([O:20][C:21]([N:23]1[CH:27]=[CH:26][CH:25]=[CH:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17].[CH3:28][C:29]1[CH:56]=[CH:55][CH:54]=[CH:53][C:30]=1[CH2:31][N:32]([CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=1[CH3:52])[C@@H:33]([CH2:36][C:37]1[CH:42]=[C:41]([F:43])[CH:40]=[C:39]([F:44])[CH:38]=1)[CH:34]=[O:35]>O1CCCC1>[C:16]([O:20][C:21]([N:23]1[CH:27]=[CH:26][CH:25]=[C:24]1[C@@H:34]([OH:35])[C@@H:33]([N:32]([CH2:31][C:30]1[CH:53]=[CH:54][CH:55]=[CH:56][C:29]=1[CH3:28])[CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=1[CH3:52])[CH2:36][C:37]1[CH:42]=[C:41]([F:43])[CH:40]=[C:39]([F:44])[CH:38]=1)=[O:22])([CH3:19])([CH3:17])[CH3:18]

참가 물질

6

반응물 4

HCID 130352,2,6,6-TetramethylpiperidineHCID 643494tert-butyl 1H-pyrrole-1-carboxylateHCID 86614992HCID 86614992, 화합물HCID 178418339Butyllithium

생성물 1

HCID 68814650HCID 68814650, 화합물수율 10%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
-10 °C

실험 절차

Add n-butyllithium (3.30 mL, 8.25 mmol, 2.5 M in hexanes) to a solution of 2,2,6,6-tetramethylpiperidine (1.40 mL, 8.18 mmol) in tetrahydrofuran (THF) (30 mL) at −78° C. over 2 min. Stir 5 min, then warm to −10° C. and stir 5 min, then cool to −78° C. Add N-tert-butoxycarbonylpyrrole (1.37 mL, 8.25 mmol) in THF (1.6 mL) over 3 min. Stir 30 min and add 2-(S)-[bis-(2-methylbenzyl)-amino]-3-(3,5-difluorophenyl)-propionaldehyde (2.96 g, 7.44 mmol) in THF (15 mL) over 5 min. Stir 60 min at −78° C., warm to 0° C. and stir 60 min. Cool −78° C. and quench with saturated aqueous ammonium chloride solution. Extract with ethyl acetate, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with hexanes and dichloromethane) to give the title compound as a foam (0.416 g, 10%).

후처리

  1. stirringstir 5 min
  2. temperaturecool to −78° C
  3. stirringStir 30 min
  4. stirringStir 60 min at −78° C.
  5. temperaturewarm to 0° C.
  6. stirringstir 60 min
  7. temperatureCool −78° C.
  8. customquench with saturated aqueous ammonium chloride solution
  9. extractionExtract with ethyl acetate
  10. dry with materialdry (magnesium sulfate)
  11. concentrationconcentrate
  12. custompurify
  13. wash(silica gel chromatography, eluting with hexanes and dichloromethane)

출처 및 근거

ORD 기록
ord-8e478015b76044cc98413c62c33f9d85
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585885B2

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