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

HRID 553028

반응식

HRID 553028 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-a417337957c34d5e9aa7f3755d9eb191
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07951791B2

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