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 1794024Notes

Reaction equation

HRID 1794024 reaction equation
[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]

Participants

5

Reactant 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

Product 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)-methanoneYield 36.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

[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.

Workup

  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

Sources & evidence

ORD record
ord-0d8f1473661a4019b460419498c3d008
Source dataset
uspto-grants-2006_04
Patent number
US07022699B2

Reaction notes

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