Phthalimide → Ethyl 4-(1,3-dioxoisoindolin-2-yl)-1-methylcyclohexanecarboxylate

HRID 1944720ノート

反応式

HRID 1944720 の反応式
O[CH:2]1[CH2:7][CH2:6][C:5]([CH3:13])([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:33]1(=[O:43])[NH:37][C:36](=[O:38])[C:35]2=[CH:39][CH:40]=[CH:41][CH:42]=[C:34]12.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[O:38]=[C:36]1[C:35]2[C:34](=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:33](=[O:43])[N:37]1[CH:2]1[CH2:7][CH2:6][C:5]([CH3:13])([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1

参加物

6

反応物 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 58230927Ethyl 4-hydroxy-1-methylcyclohexanecarboxylate2 回

生成物 1

HCID 58074352Ethyl 4-(1,3-dioxoisoindolin-2-yl)-1-methylcyclohexanecarboxylate収率 63.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Ethyl 4-hydroxy-1-methylcyclohexanecarboxylate (Intermediate 67, 930 mg, 4.99 mmol), triphenylphosphine (3.143 g, 11.98 mmol), and phthalimide (882 mg, 5.99 mmol) were dissolved in 60 mL of THF. DIAD (2.33 mL, 11.98 mmol) was then added and the reaction mixture was stirred overnight at room temperature. The mixture was concentrated under vacuum, and the residue was chromatographed on silica gel using an ethyl acetate/heptane gradient. The title compound (1 g) was obtained as a clear oil.

後処理

  1. concentrationThe mixture was concentrated under vacuum
  2. customthe residue was chromatographed on silica gel using an ethyl acetate/heptane gradient

出典と根拠

ORDレコード
ord-ca954aeb7cf542cd8f3810b5053b3583
出典データセット
uspto-grants-2013_03
特許番号
US08394858B2

反応ノート

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