Triphenylphosphine → HCID 18361591, compound

HRID 854039Notes

Reaction equation

HRID 854039 reaction equation
[ClH:1].[CH3:2][N:3]([CH2:5][CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11](NS(C3C=CC4C(=CC=CC=4)C=3)(=O)=O)[CH:12]=2)[CH2:7]1)[CH3:4].[CH2:30]([C:32]1[CH:37]=[CH:36][C:35]([C:38]2[CH:43]=[CH:42][C:41]([CH2:44][OH:45])=[CH:40][CH:39]=2)=[CH:34][CH:33]=1)[CH3:31].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[ClH:1].[CH3:4][N:3]([CH2:5][CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:45][CH2:44][C:41]3[CH:40]=[CH:39][C:38]([C:35]4[CH:36]=[CH:37][C:32]([CH2:30][CH3:31])=[CH:33][CH:34]=4)=[CH:43][CH:42]=3)[CH:12]=2)[CH2:7]1)[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 1392188HCID 1392188, compoundHCID 22998650HCID 22998650, compound

Product 1

HCID 18361591HCID 18361591, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(N,N-Dimethylamino)methyl-6-hydroxytetralin (300 mg; obtained in Reference Example 16), (4′-ethylbiphenyl-4-yl)methanol (372 mg) and triphenylphosphine (460 mg) were dissolved in THF (5 ml), to which was dropwise added diethyl azodicarboxylate (305 mg) with cooling with ice. The reaction mixture was stirred at room temperature for 4 hours, and then the solvent was evaporated out. Water was added to the residue, which was then extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, then dried, and concentrated. The residue was purified by alumina column chromatography (eluent:ethyl acetate/hexane=1/10), and then processed with a solution of 4 N hydrochloric acid-ethyl acetate to form a hydrochloride. The thus-formed salt was recrystallized from ethanol-diisopropyl ether to obtain the entitled compound (310 mg).

Workup

  1. temperaturewith cooling with ice
  2. customthe solvent was evaporated out
  3. additionWater was added to the residue, which
  4. extractionwas then extracted with ethyl acetate
  5. washThe organic layer was washed with a saturated aqueous sodium bicarbonate solution
  6. dry with materiala saturated aqueous sodium chloride solution, then dried
  7. concentrationconcentrated
  8. customThe residue was purified by alumina column chromatography (eluent:ethyl acetate/hexane=1/10)

Sources & evidence

ORD record
ord-d0de2832a6ea4ec9951f6d2800c04325
Source dataset
uspto-grants-2007_08
Patent number
US07256204B2

Reaction notes

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