Triphenylphosphine → Ammonia

HRID 2353345Notes

Reaction equation

HRID 2353345 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([OH:9])[CH2:2]2.[OH:10][C:11]1[CH:23]=[CH:22][C:14]2[O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:13]=2[CH:12]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[OH-:55].[Na+]>C1COCC1>[NH3:1].[C:14]([OH:9])(=[O:15])/[CH:13]=[CH:12]/[C:11]([OH:10])=[O:55].[CH:12]1[C:13]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[O:15][C:14]=2[CH:22]=[CH:23][C:11]=1[O:9][CH:3]1[CH:4]2[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]2)[CH2:2]1

Participants

8

Reactant 5

HCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 15381(+-)-3-QuinuclidinolHCID 665872-DibenzofuranolHCID 5462977Diethyl azodicarboxylate

Product 2

HCID 222AmmoniaHCID 66838098HCID 66838098, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of (±)-3-quinuclidinol (3.0 g, 23.6 mmol), 2-hydroxydibenzofuran (4.3 g, 23.6 mmol), triphenylphosphine (9.29 g, 35.4 mmol) and THF, was added: diethylazodicarboxylate (6.3 ml, 35.4 mmol) over a time period of 40 min at room temperature. The mixture was stirred at 50° C. for 7 days. Aqueous sodium hydroxide (100 ml, 1 M) was added. The mixture was extracted with dichloromethane (3×100 ml). Chromatography on silica gel with dichloromethane, methanol and conc. ammonia (89:10:1) gave the title compound. Yield 2.0 g (29%).

Workup

  1. additionwas added
  2. customover a time period of 40 min
  3. customat room temperature
  4. extractionThe mixture was extracted with dichloromethane (3×100 ml)

Sources & evidence

ORD record
ord-efb3dd893541464cbd2436c7d9deb1e9
Source dataset
uspto-grants-2010_07
Patent number
US07750022B2

Reaction notes

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