Sodium → 8-(1-((Tert-butyldimethylsilyl)oxy)-3-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)propan-2-yl)-2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one

HRID 1848550Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1848550
[Si:1]([O:8][CH2:9][C:10](=O)[CH2:11][C:12]1[C:13]([CH3:22])=[C:14]2[C:18](=[CH:19][CH:20]=1)[C:17](=[O:21])[O:16][CH2:15]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:24][C:25]1[C:29](=[O:30])[O:28][CH2:27][C:26]=1[N:31]1[CH2:35][CH2:34][C:33]2([CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)[C:32]1=[O:41].[Na]>CO.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[Si:1]([O:8][CH2:9][CH:10]([N:38]1[CH2:39][CH2:40][C:33]2([C:32](=[O:41])[N:31]([C:26]3[CH2:27][O:28][C:29](=[O:30])[C:25]=3[CH3:24])[CH2:35][CH2:34]2)[CH2:36][CH2:37]1)[CH2:11][C:12]1[C:13]([CH3:22])=[C:14]2[C:18](=[CH:19][CH:20]=1)[C:17](=[O:21])[O:16][CH2:15]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 5360545SodiumHCID 867095242-(4-Methyl-5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-oneHCID 867095325-(3-((tert-butyldimethylsilyl)oxy)-2-oxopropyl)-4-methylisobenzofuran-1(3H)-one

Produkt 1

HCID 867095348-(1-((Tert-butyldimethylsilyl)oxy)-3-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)propan-2-yl)-2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11026Titanium isopropoxideKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 5-(3-((tert-butyldimethylsilyl)oxy)-2-oxopropyl)-4-methylisobenzo furan-1(3H)-one (0.50 g, 1.5 mmol) in methanol (20 mL) was added 2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one (I-17) (0.45 g, 1.8 mmol) and titanium(IV) isopropoxide (2.10 g, 7.5 mmol). After stirring at for room temperature 48 h, sodium cyanoborohyride (190 mg, 3.0 mmol) was added and the reaction mixture was stirred at room temperature for 20 h. The reaction mixture was quenched with water (10 mL), and the resulting inorganic precipitate was filtered off and washed with methanol (50 mL). The filtrate was then concentrated and the crude product was dissolved in ethyl acetate, filtered to remove the remaining inorganic solids, and concentrated. The residue was purified by flash column chromatography (0-10% methanol in dichloromethane) to give the title compound. LC-MS (ESI, m/z): 569 [M+1]+

Aufarbeitung

  1. additionwas added
  2. customThe reaction mixture was quenched with water (10 mL)
  3. filtrationthe resulting inorganic precipitate was filtered off
  4. washwashed with methanol (50 mL)
  5. concentrationThe filtrate was then concentrated
  6. dissolutionthe crude product was dissolved in ethyl acetate
  7. filtrationfiltered
  8. customto remove the remaining inorganic solids
  9. concentrationconcentrated
  10. customThe residue was purified by flash column chromatography (0-10% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-1c99a32c414e47abb28550a68e258081
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952166B2

Notizen zur Reaktion

Wird geladen…