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Sodium Bicarbonate → Methyl 3-{[(2R,6R)-1-benzyl-2,6-dimethylpiperidin-4-yl]amino}-5-fluoro-2-methylbenzoate

HRID 2208677
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2208677
[NH2:1][C:2]1[C:3]([CH3:13])=[C:4]([CH:9]=[C:10]([F:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH2:14]([N:21]1[C@@H:26]([CH3:27])[CH2:25][C:24](=O)[CH2:23][C@H:22]1[CH3:29])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>C1COCC1.C(O)(C(F)(F)F)=O>[CH2:14]([N:21]1[C@H:26]([CH3:27])[CH2:25][CH:24]([NH:1][C:2]2[C:3]([CH3:13])=[C:4]([CH:9]=[C:10]([F:12])[CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])[CH2:23][C@H:22]1[CH3:29])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 53419617Methyl 3-amino-5-fluoro-2-methylbenzoateHCID 59342390(2R,6S)-1-benzyl-2,6-dimethylpiperidin-4-one

Produkt 1

HCID 70873973Methyl 3-{[(2R,6R)-1-benzyl-2,6-dimethylpiperidin-4-yl]amino}-5-fluoro-2-methylbenzoateAusbeute 30,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6422Trifluoroacetic acidLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a stirred solution of methyl 3-amino-5-fluoro-2-methylbenzoate (520 mg, 2.84 mmol) in THF (20 mL) and TFA (813 uL) was added (2R,6S)-1-benzyl-2,6-dimethylpiperidin-4-one (679 mg, 3.12 mmol) at 0° C. The mixture was stirred at 60° C. for 1 hour under nitrogen atmosphere. Then the mixture was cooled to 0° C. in an ice bath, sodium triacetoxyborohydride (1.27 g, 5.68 mmol) was added. The reaction mixture was stirred at rt for 2 hours. Then aq. NaHCO3 was added at 0° C. until pH8-9, and the content was extracted with ethylacetate. The organic layer was dried over MgSO4 and filtered. The filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (NH—SiO2; heptane/ethylacetate=5/1) to give titled compound as a colorless oil (331 mg, 30% yield.). 1H-NMR (400 MHz, CDCl3) δppm; 7.35-7.39 (m, 2H), 7.27-7.30 (m, 2H), 7.21-7.26 (m, 1H), 6.76 (dd, J=2.4, 9.2 Hz, 1H), 6.45 (dd, J=2.4, 11.2 Hz, 1H), 3.94 (d, J=14.4 Hz, 1H), 3.87 (s, 3H), 3.58-3.65 (m, 2H), 3.46 (d, J=14.4 Hz, 1H), 3.06-3.12 (m, 1H), 2.94-3.01 (m, 1H), 2.21 (s, 3H), 2.02-2.07 (m, 1H), 1.82-1.89 (m, 1H), 1.15-1.22 (m, 1H), 1.12 (d, J=6.0 Hz, 3H), 1.09 (d, J=7.2 Hz, 3H).

Aufarbeitung

  1. temperatureThen the mixture was cooled to 0° C. in an ice bath
  2. stirringThe reaction mixture was stirred at rt for 2 hours
  3. extractionthe content was extracted with ethylacetate
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (NH—SiO2; heptane/ethylacetate=5/1)

Quellen und Nachweise

ORD-Eintrag
ord-9628d1b858d04b85b588c1a98eefe12c
Quelldatensatz
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09376422B2

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