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Binap, (A+-)- → HCID 66700958、化合物

HRID 1253700
ノート
印刷プレビュー

反応式

HRID 1253700 の反応式
[CH2:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[CH2:4][CH2:3][N:2]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].Br[C:19]1[C:28]2[C:23](=[C:24]([C:29]([F:32])([F:31])[F:30])[CH:25]=[CH:26][CH:27]=2)[N:22]=[CH:21][CH:20]=1.CC([O-])(C)C.[Na+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:32][C:29]([F:30])([F:31])[C:24]1[CH:25]=[CH:26][CH:27]=[C:28]2[C:23]=1[N:22]=[CH:21][CH:20]=[C:19]2[N:8]1[CH2:7][CH2:6][C:5]2([CH2:1][N:2]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:3][CH2:4]2)[CH2:10][CH2:9]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 634876Binap, (A+-)-HCID 212773694-Bromo-8-(trifluoromethyl)quinolineHCID 23676156Sodium t-butoxideHCID 34178604tert-Butyl 2,8-diazaspiro[4.5]decane-2-carboxylate

生成物 1

HCID 66700958HCID 66700958、化合物収率 40%

試薬・触媒・溶媒 2

HCID 167845
palladium(II) acetate
触媒
HCID 1140Toluene溶媒

実験手順

A mixture of tert-butyl 2,8-diazaspiro[4.5]decane-2-carboxylate (2.5 mmol, 1.0 eq.) and 4-bromo-8-(trifluoromethyl)quinoline (2.5 mmol, 1.0 eq.) and tBuONa (7.5 mmol, 3.0 eq.) in toluene (12 ml) was degassed with argon for 10 min. BINAP (0.15 mmol, 0.06 eq.) and Pd(OAc)2 (0.05 mmol, 0.02 eq.) were added and the reaction mixture obtained was heated under reflux for 14 h. The reaction mixture was filtered over Celite and the filtrate was concentrated in vacuo in order to obtain the crude product, which was purified by column chromatography (silica gel, 22-25% ethyl acetate in hexane), in order to obtain the desired product. Yield: 40%

後処理

  1. customwas degassed with argon for 10 min
  2. customthe reaction mixture obtained
  3. temperaturewas heated
  4. temperatureunder reflux for 14 h
  5. filtrationThe reaction mixture was filtered over Celite
  6. concentrationthe filtrate was concentrated in vacuo in order
  7. customto obtain the crude product, which
  8. customwas purified by column chromatography (silica gel, 22-25% ethyl acetate in hexane), in order

出典と根拠

ORDレコード
ord-9601748f395e441dbd3c80c3e9a2a858
出典データセット
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08455475B2

反応ノート

読み込み中…

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