2,2,6,6-Tetramethylpiperidine → HCID 68814650、化合物

HRID 732343

反応式

HRID 732343 の反応式
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]

参加物

6

反応物 4

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

生成物 1

HCID 68814650HCID 68814650、化合物収率 10%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-10 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-8e478015b76044cc98413c62c33f9d85
出典データセット
uspto-grants-2009_09
特許番号
US07585885B2

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