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Triacetoxyperiodinane → (S)-Ethyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-formyl-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate

HRID 921102
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 921102
[CH2:1]([O:4][C:5]1([CH3:34])[CH2:10][CH2:9][N:8]([C:11]2[N:16]3[N:17]=[C:18]([CH2:20][OH:21])[CH:19]=[C:15]3[N:14]=[C:13]([CH3:22])[C:12]=2[C@H:23]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:7][CH2:6]1)[CH:2]=[CH2:3].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH2:1]([O:4][C:5]1([CH3:34])[CH2:10][CH2:9][N:8]([C:11]2[N:16]3[N:17]=[C:18]([CH:20]=[O:21])[CH:19]=[C:15]3[N:14]=[C:13]([CH3:22])[C:12]=2[C@H:23]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:7][CH2:6]1)[CH:2]=[CH2:3]
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Komponenten

4

Edukt 2

HCID 159087TriacetoxyperiodinaneHCID 118318735(S)-Ethyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(hydroxymethyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate

Produkt 1

HCID 118318786(S)-Ethyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-formyl-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetateAusbeute 71,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

To a solution of (S)-ethyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(hydroxymethyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (0.2747 g, 0.579 mmol) in wet DCM (5 mL) was added Dess-Martin periodinane (0.319 g, 0.752 mmol) and the mixture was stirred at room temperature. After 3 h, the solids were removed by filtration. The filtrate was washed with aq Na2S2O3, dried (Na2SO4), filtered and concentrated. The resulting oil was purified by flash chromatography (Biotage; 0%-50% EtOAc/hexane; 10 CV) to give the title compound (0.1962 g, 0.415 mmol, 71.7% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 10.17 (s, 1H), 7.02 (s, 1H), 6.19-5.98 (m, 1H), 5.96-5.76 (m, 1H), 5.57-5.37 (m, 2H), 5.24 (dd, J=10.4, 1.6 Hz, 1H), 4.24 (dd, J=15.9, 7.1 Hz, 2H), 4.03 (d, J=4.9 Hz, 2H), 2.65 (s, 3H), 2.08-1.93 (m, 5H), 1.81-1.66 (m, 1H), 1.37 (s, 3H), 1.29-1.25 (m, 12H). 2 piperidine protons not seen by NMR. LCMS (M+H) calcd for C25H37N4O5: 473.27. found: 473.3.

Aufarbeitung

  1. customthe solids were removed by filtration
  2. washThe filtrate was washed with aq Na2S2O3
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting oil was purified by flash chromatography (Biotage; 0%-50% EtOAc/hexane; 10 CV)

Quellen und Nachweise

ORD-Eintrag
ord-0825a6ab5f024857b09737c36297f6e9
Quelldatensatz
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09273067B2

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