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

HRID 1944720노트

반응식

HRID 1944720 반응식
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

참가 물질

6

반응물 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 58230927Ethyl 4-hydroxy-1-methylcyclohexanecarboxylate2회

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-ca954aeb7cf542cd8f3810b5053b3583
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394858B2

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