Triphenylphosphine → HCID 22928404, compound

HRID 751465Notes

Reaction equation

HRID 751465 reaction equation
[N:1]([CH:4]1[CH2:10][C:9]([CH3:12])([CH3:11])[CH2:8][N:7]([S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)(=[O:15])=[O:14])[CH2:6][CH:5]1[OH:22])=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1.O>[NH2:1][CH:4]1[CH2:10][C:9]([CH3:12])([CH3:11])[CH2:8][N:7]([S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)(=[O:15])=[O:14])[CH2:6][CH:5]1[OH:22]

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 22928354HCID 22928354, compound

Product 1

HCID 22928404HCID 22928404, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

4-Azido-6,6-dimethyl-1-(pyridine-2-sulfonyl)-azepan-3-ol from Example 92f (0.4 g, 1.23 mmol) was dissolved in THF (50 ml) and H2O (0.2 ml). PPh3 (0.48 g, 1.85 mmol) was added to this solution. The reaction mixture was stirred at 45° C. over night. TLC showed no starting material left. THF was evaporated, azeotroped with toluene (2×'s). The resulting thick oil was dissolved in MeOH, treated with HCl in ether to adjust pH to acidic. More ether was added and the solution turned cloudy. 0.22 g white precipitate of the title compound was collected. (45% yield); 1H-NMR (400 MHz, CD3OD): •8.68(m, 1H), 8.10-7.93(m, 2H), 7.62(m, 1H), 3.90(m, 1H), 3.68(m, 1H), 3.40-2.90(m, 4H), 1.82(m, 1H), 1.53(d, 1H), 1.05(s, 6H)

Workup

  1. waitleft
  2. customTHF was evaporated
  3. customazeotroped with toluene (2×'s)
  4. dissolutionThe resulting thick oil was dissolved in MeOH
  5. additiontreated with HCl in ether
  6. additionMore ether was added
  7. custom0.22 g white precipitate of the title compound was collected

Sources & evidence

ORD record
ord-2f78898002ea4b79bb1f8a2a40fe2631
Source dataset
uspto-grants-2008_07
Patent number
US07405209B2

Reaction notes

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