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Triethylamine → Methyl 5-(9-(3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecane-4-carbonyl)thiophene-2-carboxylate

HRID 471032
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 471032
FC(F)(F)C(O)=O.[O:8]1[C:13]2([CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH2:12][N:11]([C:19]([C:21]2[S:25][C:24]([C:26]([O:28][CH3:29])=[O:27])=[CH:23][CH:22]=2)=[O:20])[CH2:10][CH2:9]1.Br[CH2:31][C:32]1[CH:33]=[C:34]([CH2:38][CH2:39][OH:40])[CH:35]=[CH:36][CH:37]=1.C(N(CC)CC)C>C(#N)C>[OH:40][CH2:39][CH2:38][C:34]1[CH:33]=[C:32]([CH:37]=[CH:36][CH:35]=1)[CH2:31][N:16]1[CH2:17][CH2:18][C:13]2([O:8][CH2:9][CH2:10][N:11]([C:19]([C:21]3[S:25][C:24]([C:26]([O:28][CH3:29])=[O:27])=[CH:23][CH:22]=3)=[O:20])[CH2:12]2)[CH2:14][CH2:15]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 18999576Benzeneethanol, 3-(bromomethyl)-HCID 67292236Methyl 5-(1-oxa-4,9-diazaspiro[5.5]undecane-4-carbonyl)thiophene-2-carboxylate trifluoroacetate

Produkt 1

HCID 57989150Methyl 5-(9-(3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecane-4-carbonyl)thiophene-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342
Acetonitrile
Lösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A solution of methyl 5-(1-oxa-4,9-diazaspiro[5.5]undecane-4-carbonyl)thiophene-2-carboxylate trifluoroacetate (example 30, step b) (0.46 g) and 2-(3-(bromomethyl)phenyl)ethanol (example 6, step a) (0.226 g) in acetonitrile (10 mL) was treated with triethylamine (0.44 mL) and the mixture stirred at 20° C. for 2 hours. The solvent was evaporated under reduced pressure and the residue partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic layer was dried over sodium sulphate, filtered and the solvent evaporated under reduced pressure. The crude product was purified by flash silica chromatography using 1% triethylamine and 3% methanol in dichloromethane as solvent. Pure fractions were evaporated to dryness to afford the subtitled compound. Yield 0.41 g.

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue partitioned between ethyl acetate and saturated sodium bicarbonate solution
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure
  6. customThe crude product was purified by flash silica chromatography
  7. customPure fractions were evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-1b04b597b15f4200869e22e5b71dd5d7
Quelldatensatz
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08629271B2

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