Triphenylphosphine → HCID 58993691, compound

HRID 391382Notes

Reaction equation

HRID 391382 reaction equation
[C:1]1([C:7]2([CH2:20][O:21][CH2:22][C:23]3[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[C:25]([NH:33][C:34](=O)[C:35]([F:38])([F:37])[F:36])[CH:24]=3)[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N-:59]=[N+:60]=[N-:61].[Na+]>C(Cl)(Cl)(Cl)Cl>[C:1]1([C:7]2([CH2:20][O:21][CH2:22][C:23]3[CH:24]=[C:25]([N:33]4[C:34]([C:35]([F:37])([F:38])[F:36])=[N:61][N:60]=[N:59]4)[CH:26]=[C:27]([C:29]([F:31])([F:30])[F:32])[CH:28]=3)[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:14])[CH2:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 33557Sodium AzideHCID 58993625HCID 58993625, compound

Product 1

HCID 58993691HCID 58993691, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

tert-Butyl 4-phenyl-4-((3-(2,2,2-trifluoroacetamido)-5-(trifluoromethyl)benzyloxy)methyl)piperidine-1-carboxylate (100 mg, 0.18 mmol) in carbon tetrachloride (3 mL) was treated with triphenylphosphine (117 mg, 0.45 mmol) and heated at reflux overnight. After cooling to room temperature, the reaction was concentrated and the residue dissolved in dimethylformamide (2 mL). The mixture was treated with sodium azide (25 mg, 0.37 mmol) and stirred at room temperature for 5 h. The solvents were evaporated and the crude product purified by flash chromatography on silica gel (30% ethyl acetate/hexanes) to afford 46 mg (45%). 1H-NMR (CDCl3, 500 MHz) δ 7.61 (s, 1H), 7.59 (s, 1H), 7.30-7.32 (m, 2H), 7.23-7.26 (m, 2H), 7.12 (s, 1H), 7.05-7.08 (m, 1H), 4.51 (s, 2H), 3.74 (m, 2H), 3.46 (s, 2H), 2.99-3.03 (m, 2H), 2.21-2.24 (m, 2H), 1.79-1.84 (m, 2H), 1.42 (s, 9H). Mass spec.: 608.16 (MNa)+.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. concentrationthe reaction was concentrated
  4. dissolutionthe residue dissolved in dimethylformamide (2 mL)
  5. customThe solvents were evaporated
  6. customthe crude product purified by flash chromatography on silica gel (30% ethyl acetate/hexanes)
  7. customto afford 46 mg (45%)

Sources & evidence

ORD record
ord-a2865cfaad284bbfa22b4430154d025c
Source dataset
uspto-grants-2013_02
Patent number
US08383821B2

Reaction notes

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