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Sodium Iodide → (S)-tert-butyl 5-((3-fluoropyrrolidin-1-yl)methyl)pyridin-2-ylcarbamate

HRID 520497
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HRID 520497 반응식
Cl[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[N:7][CH:8]=1.[F:17][C@H:18]1[CH2:22][CH2:21][NH:20][CH2:19]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C=O)C>[F:17][C@H:18]1[CH2:22][CH2:21][N:20]([CH2:2][C:3]2[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[N:7][CH:8]=2)[CH2:19]1
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참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 7016277(S)-3-fluoropyrrolidineHCID 67993136Tert-butyl (5-chloromethylpyridin-2-yl)carbamate

생성물 1

HCID 67993091(S)-tert-butyl 5-((3-fluoropyrrolidin-1-yl)methyl)pyridin-2-ylcarbamate수율 61%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

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온도
60 °C

실험 절차

A mixture of tert-butyl 5-(chloromethyl)pyridin-2-ylcarbamate 117(9.5 g, 39.1 mmol), (S)-3-fluoropyrrolidine 118 (4.19 g, 47.0 mmol), potassium carbonate (16.2 g, 117 mmol) and sodium iodide (0.586 g, 3.91 mmol) in DMF (150 mL) was stirred at 60° C. for 2 h. The reaction mixture was filtered, and the filtrate was concentrated in vacuo. H2O (250 mL) was added and the resulting solid was collected by filtration, rinsed with H2O and dried to give 119 (7.00 g, 61% yield).

후처리

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. additionH2O (250 mL) was added
  4. filtrationthe resulting solid was collected by filtration
  5. washrinsed with H2O
  6. customdried

출처 및 근거

ORD 기록
ord-1f6e0445f1c94379b5054b101ebbfe4e
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09326986B2

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