Triphenylphosphine → 2-[(3S)-1-azabicyclo[2.2.2]octan-3-yloxy]-fluoren-9-one

HRID 553028

Reaction equation

HRID 553028 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:15])[C:4]=2[CH:3]=1.[N:16]12[CH2:23][CH2:22][CH:19]([CH2:20][CH2:21]1)[C@@H:18](O)[CH2:17]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[N:16]12[CH2:23][CH2:22][CH:19]([CH2:20][CH2:21]1)[C@H:18]([O:1][C:2]1[CH:14]=[CH:13][C:12]3[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[C:5](=[O:15])[C:4]=3[CH:3]=1)[CH2:17]2

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 813862-Hydroxyfluoren-9-oneHCID 914043-Quinuclidinol, (-)-HCID 5462977Diethyl azodicarboxylate

Product 1

HCID 112204662-[(3S)-1-azabicyclo[2.2.2]octan-3-yloxy]-fluoren-9-oneYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. mixture of 2-hydroxyfluoren-9-one (196 mg, 1.00 mmol; Aldrich), (3R)-quinuclidin-3-ol (151 mg, 1.20 mmol; Acros), and polymer-bound triphenylphosphine (500 mg, 3 mmol/g; Aldrich) in THF (5 mL) was added diethylazodicarboxylate (200 μL, 1.27 mmol; Aldrich). After 1 h, the reaction mixture was allowed to warm to room temperature and was stirred overnight (16 h). The mixture was filtered through diatomaceous earth, the filter pad rinsed with dichloromethane, and the organic extracts purified twice by flash chromatography (80 g silica gel, eluting with 1-5% of 10% NH4OH/MeOH in CH2Cl2) to afford the title compound (104 mg, 0.340 mmol, 34% yield). MS (DCI/NH3): m/z 306 (M+1)+.

Workup

  1. filtrationThe mixture was filtered through diatomaceous earth
  2. washthe filter pad rinsed with dichloromethane
  3. customthe organic extracts purified twice by flash chromatography (80 g silica gel, eluting with 1-5% of 10% NH4OH/MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-a417337957c34d5e9aa7f3755d9eb191
Source dataset
uspto-grants-2011_05
Patent number
US07951791B2

Linked notes

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