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Triphenylphosphine → [4-(3-Amino-2-methyl-cyclohex-1-en-1-yl)-3-methyl-phenyl]-(10,11-dihydro-5H-pyrrolo[2,1-c](1,4]benzodiazepin-10-yl)-methanone

HRID 1794024
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HRID 1794024 반응식
[N:1]([CH:4]1[CH2:9][CH2:8][CH2:7][C:6]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([N:18]3[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[CH2:22][N:21]4[CH:29]=[CH:30][CH:31]=[C:20]4[CH2:19]3)=[O:17])=[CH:12][C:11]=2[CH3:32])=[C:5]1[CH3:33])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.O>[NH2:1][CH:4]1[CH2:9][CH2:8][CH2:7][C:6]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([N:18]3[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[CH2:22][N:21]4[CH:29]=[CH:30][CH:31]=[C:20]4[CH2:19]3)=[O:17])=[CH:12][C:11]=2[CH3:32])=[C:5]1[CH3:33]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 11776TriphenylphosphineHCID 10225076[4-(3-Azido-2-methyl-cyclohex-1-en-1-yl)-3-methyl-phenyl]-(10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-methanone

생성물 1

HCID 10158554[4-(3-Amino-2-methyl-cyclohex-1-en-1-yl)-3-methyl-phenyl]-(10,11-dihydro-5H-pyrrolo[2,1-c](1,4]benzodiazepin-10-yl)-methanone수율 36.7%

시약·촉매·용매 2

HCID 962Water용매
HCID 8028
Tetrahydrofuran
용매

실험 절차

[4-(3-Azido-2-methyl-cyclohex-1-en-1-yl)-3-methyl-phenyl]-(10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-methanone of Step A (0.290 g, 0.663 mmol) was dissolved in 7 mL of a 10:1 mixture of tetrahydrofuran and water. Polymer-supported triphenylphosphine (0.287 g, approximately 0.862 mmol) was added and the reaction stirred at room temperature overnight. The mixture was filtered and concentrated, and the residue purified by flash column chromatography on silica gel, eluting with 3% ammonium hydroxide and 20% methanol in chloroform. A yellow oil was isolated which was triturated with 1:1 diethyl ether/petroleum ether to afford the title compound (0.100 g) as a white solid.

후처리

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. customthe residue purified by flash column chromatography on silica gel
  4. washeluting with 3% ammonium hydroxide and 20% methanol in chloroform
  5. customA yellow oil was isolated which
  6. customwas triturated with 1:1 diethyl ether/petroleum ether

출처 및 근거

ORD 기록
ord-0d8f1473661a4019b460419498c3d008
출처 데이터셋
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07022699B2

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