Propionic Acid → 1-(2,8-Dimethyl-1-thia-3,8-diaza-spiro[4.5]dec-3-yl)-propan-1-one

HRID 574625Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 574625
[CH3:1][CH:2]1[NH:6][CH2:5][C:4]2([CH2:11][CH2:10][N:9]([CH3:12])[CH2:8][CH2:7]2)[S:3]1.C1(N=C=NC2CCCCC2)CCCCC1.[C:28](O)(=[O:31])[CH2:29][CH3:30]>ClCCl>[CH3:1][CH:2]1[N:6]([C:28](=[O:31])[CH2:29][CH3:30])[CH2:5][C:4]2([CH2:11][CH2:10][N:9]([CH3:12])[CH2:8][CH2:7]2)[S:3]1

Komponenten

5

Edukt 3

HCID 1032Propionic AcidHCID 10868DicyclohexylcarbodiimideHCID 669939622,8-Dimethyl-1-thia-3,8-diazaspiro[4.5]decane

Produkt 1

HCID 468468051-(2,8-Dimethyl-1-thia-3,8-diaza-spiro[4.5]dec-3-yl)-propan-1-oneAusbeute 44,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 2,8-dimethyl-1-thia-3,8-diaza-spiro[4.5]decane (Example 1) (0.86 g, 4.62 mmol) in dichloromethane (90 ml) at room temperature was added dicyclohexylcarbodiimide (DCC) (1.28 g, 6.2 mmol) followed by addition of propionic acid (0.41 ml, 5.5 mmol). The resulting solution was stirred at room temperature overnight. During the reaction a white solid precipitated. After filtration the solvent was evaporated and the crude product was purified by flash chromatography (silica, CH2Cl2/MeOH/NH4OH 90/10/1) to give the title compound (0.5 g) as a colorless oil. 1H NMR (CDCl3, 300 MHz) δ 5.51, 5.19 (2q, J=6.15 and J=6.22 Hz, 1H, CHCH3), 4.63, 3.74 (2d, J=11.88 and J=11.57 Hz, 1H, CHHNCO), 3.44, 3.08 (2d, J=11.55 and J=12.09 Hz, 1H, CHHNCO), 2.8-2.6 (m, 2H), 2.5-2.2 (m, 7H, CH2, CH2CH3, NCH3), 2.2-2.0 (m, 1H), 2.0-1.8 (m, 3H) 1.52, 1.48 (2d, J=6.30 and J=6.18 Hz, 3H, CH3—CH), 1.19-1.12 (m, 3H, CH3) ppm; 13C NMR (CDCl3, 300 MHz) δ 171.6 (C), 57.5, 57.2 (CH), 55.5 (C), 54.7, 54.3 (CH2), 53.2, 53.0 (CH2), 46.3 (CH3), 38.4, 37.7 (CH2), 37.0, 36.4 (CH2), 28.8, 26.8 (CH2), 25.6, 23.6 (CH3), 9.6, 9.4 (CH3) ppm.

Aufarbeitung

  1. customDuring the reaction a white solid
  2. customprecipitated
  3. filtrationAfter filtration the solvent
  4. customwas evaporated
  5. customthe crude product was purified by flash chromatography (silica, CH2Cl2/MeOH/NH4OH 90/10/1)

Quellen und Nachweise

ORD-Eintrag
ord-7784dd8a4e204aafb18b04ab26a613b3
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09034891B2

Notizen zur Reaktion

Wird geladen…