Phthalimide → HCID 1296952, 화합물

HRID 1360190노트

반응식

HRID 1360190 반응식
[C@H:1]12[CH2:7][C@H:4]([CH2:5][CH2:6]1)[CH2:3][C@@H:2]2O.[C:9]1(=[O:19])[NH:13][C:12](=[O:14])[C:11]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:10]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[C@H:1]12[CH2:7][C@H:4]([CH2:5][CH2:6]1)[CH2:3][C@H:2]2[N:13]1[C:9](=[O:19])[C:10]2[C:11](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:12]1=[O:14]

참가 물질

6

반응물 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 10975445endo-Norborneol

생성물 1

HCID 1296952HCID 1296952, 화합물수율 65.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (1R,2S,4S)-bicyclo[2.2.1]heptane-2-ol (1.0 g) in tetrahydrofuran (10 ml) were added phthalimide (1.4 g) and triphenylphosphine (2.6 g), and diethylazodicarboxylate (1.5 ml) dropwise under ice cooling. The mixture was warmed to ambient temperature and stirred for 24 hours. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate)=100:0 to 95:5) to obtain 2-[(1R,2R,4S)-bicyclo[2.2.1]hept-2-yl]-1H-isoindole-1,3(2H)-dione (1.4 g) as a colorless solid.

후처리

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate)=100:0 to 95:5)

출처 및 근거

ORD 기록
ord-86b7f939950a428da1dc2a45d7cf67e9
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879844B2

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