Cesium carbonate → (1,4,6,7-Tetrahydro-pyrazolo[4,3-c]pyridin-5-yl)acetic acid benzyl ester

HRID 1777757Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1777757
[NH:1]1[C:9]2[CH2:8][CH2:7][NH:6][CH2:5][C:4]=2[CH:3]=[N:2]1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:17][C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]>CC#N>[CH2:21]([O:20][C:18](=[O:19])[CH2:17][N:6]1[CH2:7][CH2:8][C:9]2[NH:1][N:2]=[CH:3][C:4]=2[CH2:5]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 62576Benzyl bromoacetateHCID 27605834,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine

Produkt 1

HCID 89726571(1,4,6,7-Tetrahydro-pyrazolo[4,3-c]pyridin-5-yl)acetic acid benzyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine (300 mg) in MeCN (10 mL) was added Cs2CO3 (1.49 g) followed by benzyl bromoacetate (0.253 mL). The reaction mixture was stirred at RT overnight and evaporated to dryness. The residue was taken up in EA and washed with water and brine. The aq. layers were extracted with EA, the combined org. layers were dried (MgSO4), filtered off and evaporated in vacuo. The residue was purified by CC (Biotage, SNAP 10 g cartridge, solvent A: DCM; solvent B: DCM/MeOH 8/2; gradient in % B: 15 for 7CV, 15 to 25 over 3CV, 25 for 5CV) to afford (1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-5-yl)acetic acid benzyl ester (218 mg, pale yellow oil). LC-MS (B): tR=0.50 min; [M+H]+: 272.12. 1H-NMR (CDCl3): 7.40-7.33 (m, 5H); 7.30 (s, 1H); 5.21 (s, 2H); 3.73 (s, 2H); 3.52 (s, 2H); 3.50 (s, 1H); 2.98 (t, 2H, 6.0 Hz); 2.85 (t, 2H, 5.8 Hz).

Aufarbeitung

  1. customevaporated to dryness
  2. washwashed with water and brine
  3. extractionThe aq. layers were extracted with EA
  4. dry with materiallayers were dried (MgSO4)
  5. filtrationfiltered off
  6. customevaporated in vacuo
  7. customThe residue was purified by CC (Biotage, SNAP 10 g cartridge, solvent A: DCM; solvent B: DCM/MeOH 8/2; gradient in % B: 15 for 7CV, 15 to 25 over 3CV, 25 for 5CV)

Quellen und Nachweise

ORD-Eintrag
ord-efec05a195c042e2998f9d90e0acfd03
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09266876B2

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