Triethylamine → 3-Methyl-1-(5-nitro-pyridin-2-ylmethyl)azetidin-3-ol

HRID 55889Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 55889
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10]OS(C)(=O)=O)=[N:8][CH:9]=1)([O-:3])=[O:2].[CH3:16][C:17]1([OH:21])[CH2:20][NH:19][CH2:18]1.C(N(CC)CC)C>CO.CO.C1COCC1>[CH3:16][C:17]1([OH:21])[CH2:20][N:19]([CH2:10][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=2)[CH2:18]1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 115427823-Methylazetidin-3-olHCID 86641144Methanesulfonic acid 5-nitro-pyridin-2-ylmethyl ester

Produkt 1

HCID 903591743-Methyl-1-(5-nitro-pyridin-2-ylmethyl)azetidin-3-olAusbeute 71,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 21899815MeOH tetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 52 (0.5 g, 2.2 mmol) in MeOH (25 mL) was added Ambersep-900 OH resin (50 g) filtered to separate the resin and concentrated to obtain the free base. The free base was dissolved in MeOH-THF (10 mL, 1:1) and cooled to 0° C. 3-methyl-azetidin-3-ol (0.53 g, 4.3 mmol) and triethylamine (0.7 mL, 4.3 mmol) were added and the reaction mixture warmed to rt and stirred for 16 h. The reaction mixture was concentrated and the crude compound was purified by silica gel column chromatography (100-200 mesh), eluting with 3% MeOH/CHCl3 to give the desired compound (0.35 g, 48%, over two steps) as a pale yellow liquid. Rf: 0.3 (10% MeOH/DCM); (m/z): 224 [MH]+; 1H NMR (400 MHz, DMSO-d6): δ 9.27 (1H, d, J=2.4 Hz), 8.56 (1H, dd, J=8.8, 2.8 Hz), 7.64 (1H, d, J=8.8 Hz), 5.22 (1H, s), 3.85 (2H, s), 3.36-3.26 (2H, m), 3.02-3.00 (2H, m), 1.38 (3H, s).

Aufarbeitung

  1. filtrationfiltered
  2. customto separate the resin
  3. concentrationconcentrated
  4. customto obtain the free base
  5. temperaturethe reaction mixture warmed to rt
  6. concentrationThe reaction mixture was concentrated
  7. customthe crude compound was purified by silica gel column chromatography (100-200 mesh)
  8. washeluting with 3% MeOH/CHCl3

Quellen und Nachweise

ORD-Eintrag
ord-155fd89aab6849cea7b77783367c4e9c
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09433622B2

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