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Diisopropylethylamine → 5-Chloro-2-{(S)-1-[(3R,4S)-4-(4-chloro-3-fluoro-phenyl)-pyrrolidin-3-yl]-ethoxy}-pyridine

HRID 559300
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인쇄 미리보기

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HRID 559300 반응식
C([N:8]1[CH2:12][C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([F:20])[CH:14]=2)[C@@H:10]([C@@H:21]([O:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][N:25]=2)[CH3:22])[CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O.CCN(C(C)C)C(C)C>C1(C)C=CC=CC=1>[Cl:30][C:27]1[CH:28]=[CH:29][C:24]([O:23][C@H:21]([C@@H:10]2[C@@H:11]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([F:20])[CH:14]=3)[CH2:12][NH:8][CH2:9]2)[CH3:22])=[N:25][CH:26]=1
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참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 5213051-Chloroethyl chloroformateHCID 669992022-{(S)-1-[(3R,4S)-1-benzyl-4-(4-chloro-3-fluoro-phenyl)-pyrrolidin-3-yl]-ethoxy}-5-chloro-pyridine

생성물 1

HCID 575763605-Chloro-2-{(S)-1-[(3R,4S)-4-(4-chloro-3-fluoro-phenyl)-pyrrolidin-3-yl]-ethoxy}-pyridine수율 96%

시약·촉매·용매 1

HCID 1140
Toluene
용매

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온도
100 °C

실험 절차

To a solution of 2-{(S)-1-[(3R,4S)-1-benzyl-4-(4-chloro-3-fluoro-phenyl)-pyrrolidin-3-yl]-ethoxy}-5-chloro-pyridine 98 mg (0.22 mmol) dissolved in toluene (5 mL) were added 0.072 mL (0.66 mmol) of 1-chloroethyl chloroformate and 0.11 mL (0.66 mL) of Hunig's base. The reaction mixture was heated at 100° C. for one hour. After cooling down to RT, volatiles were removed under vacuo and the crude was dissolved in MeOH (5 mL). The reaction mixture was heated at 85° C. for 30 minutes and after cooling down to RT, volatiles were removed under vacuo and the residue was directly purified on column chromatography (SiO2, CH2Cl2/MeOH 9:1) yielded 75 mg (95%) of the title compound as a light yellow oil. ES-MS m/e: 355.1 (M+H+).

후처리

  1. temperatureAfter cooling down to RT
  2. customvolatiles were removed under vacuo
  3. dissolutionthe crude was dissolved in MeOH (5 mL)
  4. temperatureThe reaction mixture was heated at 85° C. for 30 minutes
  5. temperatureafter cooling down to RT
  6. customvolatiles were removed under vacuo
  7. customthe residue was directly purified on column chromatography (SiO2, CH2Cl2/MeOH 9:1)

출처 및 근거

ORD 기록
ord-9d942edfb4e34980bae3b2074f6acef1
출처 데이터셋
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08063075B2

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