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2-Fluoroethanol → 2-[4-[2-Fluoro-5-(2-fluoroethoxyl)phenyl]-2-pyridyl]-7-methyl-1,7-diazaspiro[4.4]nonan-6-one

HRID 2207677
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HRID 2207677 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][N:12]=[C:11]([C@H:15]2[CH2:19][CH2:18][C@@:17]3([CH2:23][CH2:22][N:21]([CH3:24])[C:20]3=[O:25])[NH:16]2)[CH:10]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.[F:61][CH2:62][CH2:63]O>C1COCC1.C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:63][CH2:62][F:61])=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][N:12]=[C:11]([CH:15]2[CH2:19][CH2:18][C:17]3([CH2:23][CH2:22][N:21]([CH3:24])[C:20]3=[O:25])[NH:16]2)[CH:10]=1
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참가 물질

7

반응물 4

HCID 97372-FluoroethanolHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 89649657(2R,5S)-2-[4-(2-fluoro-5-hydroxy-phenyl)-2-pyridyl]-7-methyl-1,7-diazaspiro[4.4]nonan-6-one

생성물 1

HCID 1317359292-[4-[2-Fluoro-5-(2-fluoroethoxyl)phenyl]-2-pyridyl]-7-methyl-1,7-diazaspiro[4.4]nonan-6-one

시약·촉매·용매 2

HCID 1140Toluene용매
HCID 8028Tetrahydrofuran용매

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온도
120 °C

실험 절차

To a Smith microwave vial was added (2R,5S)-2-[4-(2-fluoro-5-hydroxy-phenyl)-2-pyridyl]-7-methyl-1,7-diazaspiro[4.4]nonan-6-one (which may be prepared as described in Description 134) (66.5 mg, 0.1900 mmol), triphenyl phosphine (102.19 mg, 0.3900 mmol), Di-tert-butyl azodicarboxylate ((89.71 mg, 0.3900 mmol) and 2-fluoroethanol (0.02 mL, 0.2900 mmol) in THF (0.5000 mL). Toluene (1 mL) was added. The reaction mixture was heated by microwave at 120° C. for 45 min. The reaction mixture was eluted on an SCX-2 cartrige (0.5 g) and washed with DCM followed MeOH. The desired product was eluted off the cartridge with ammonia in MeOH (0.2M). Evaporation of solvents gave colourless oil. The crude residue was purified by silica gel chromatography (KPNH silica 11 g) eluting with ethyl acetate in iso-hexane (10-100%) followed by methanol in ethyl acetate (0-18%). Evaporation of desired fractions gave colourless oil. It was further purified by a ChiralPak IA column eluting with ethanol/n-heptane (20%:80%) to give 2R,5S)-2-[4-[2-fluoro-5-(2-fluoroethoxyl)phenyl]-2-pyridyl]-7-methyl-1,7-diazaspiro[4.4]nonan-6-one;

후처리

  1. washThe reaction mixture was eluted on an SCX-2 cartrige (0.5 g)
  2. washwashed with DCM
  3. washThe desired product was eluted off the cartridge with ammonia in MeOH (0.2M)
  4. customEvaporation of solvents
  5. customgave colourless oil
  6. customThe crude residue was purified by silica gel chromatography (KPNH silica 11 g)
  7. washeluting with ethyl acetate in iso-hexane (10-100%)
  8. customEvaporation of desired fractions
  9. customgave colourless oil
  10. customIt was further purified by a ChiralPak IA column
  11. washeluting with ethanol/n-heptane (20%:80%)

출처 및 근거

ORD 기록
ord-17edaf9f88644ef78aeec144ef89c9b8
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09376436B2

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