StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Acetic Acid → tert-Butyl 7-[(5-methoxypyridin-2-yl)acetyl]-2,7-diazaspiro[3.5]nonane-2-carboxylate

HRID 1913448
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1913448
Cl.[CH2:2]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[CH2:4][N:3]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].C([N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])C.[C:25]([OH:28])(=O)[CH3:26].CN([C:32]([O:36]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl[CH2:54]Cl>>[CH3:32][O:36][C:22]1[CH:54]=[CH:24][C:23]([CH2:26][C:25]([N:8]2[CH2:7][CH2:6][C:5]3([CH2:4][N:3]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:2]3)[CH2:10][CH2:9]2)=[O:28])=[N:20][CH:21]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 5

HCID 176Acetic AcidHCID 6344DichloromethaneHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 24820549tert-Butyl 2,7-diazaspiro[3.5]nonane-2-carboxylate hydrochloride

Produkt 1

HCID 58438449
tert-Butyl 7-[(5-methoxypyridin-2-yl)acetyl]-2,7-diazaspiro[3.5]nonane-2-carboxylate
Ausbeute 96 %

Versuchsvorschrift

In an oven dried round-bottomed flask was suspended tert-butyl 2,7-diazaspiro[3.5]nonane-2-carboxylate hydrochloride (1.89 g, 7.18 mmol) in anhydrous dichloromethane (50 mL). Triethylamine (2 mL, 14.4 mmol) followed by 5-methoxypyridin-2-yl)acetic acid (SM-1aa, 1.2 g, 7.18 mmol) were added. HATU (3.28 g, 8.62 mmol) was added and the resulting bright yellow solution was stirred at room temperature for 15 hours. The reaction mixture was washed consecutively with saturated aqueous sodium bicarbonate, water and brine and was dried over anhydrous MgSO4. Filtration and solvent removal afforded the crude material as a brownish oil (4.8 g). The product was purified by silica chromatography using a Combiflash ISCO (Teledyne Isco Inc., Lincoln, Nebr.) system to give the title compound (2-1a) as a light yellow foam (2.57 g, 96%). MS (ES+) 376.4 (M+H)+. 1H NMR (CDCl3) δ 1.42 (s, 9H), 1.57-1.61 (m, 2H), 1.65-1.69 (m, 2H), 3.47-3.54 (m, 4H), 3.58-3.64 (m, 4H), 3.83 (s, 3H), 3.85 (s, 2H), 7.15-7.18 (m, 1H), 7.23-7.26 (m, 1H), 8.18 (d, 1H).

Aufarbeitung

  1. customIn an oven dried round-bottomed flask was suspended
  2. additionwere added
  3. washThe reaction mixture was washed consecutively with saturated aqueous sodium bicarbonate, water and brine
  4. dry with materialwas dried over anhydrous MgSO4
  5. filtrationFiltration and solvent removal
  6. customafforded the crude material as a brownish oil (4.8 g)
  7. customThe product was purified by silica chromatography

Quellen und Nachweise

ORD-Eintrag
ord-af08487eb50c404f843080a2cfb984a0
Quelldatensatz
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08609680B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion