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

Sodium hydride → N-Boc-O-(2,2,5,5-tetramethyl-1-cyclopentyl)-1-amino-1-hydroxymethylcyclopropane

HRID 1731685
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1731685
[CH3:1][C:2]1([CH3:10])[CH2:6][CH2:5][C:4]([CH3:8])([CH3:7])[CH:3]1[OH:9].[H-].[Na+].C1OCCOCCOCCOCCOCCOC1.CCOCC.S(O)(=O)(=O)C.[C:41]([NH:48][C:49]1([CH2:52]O)[CH2:51][CH2:50]1)([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42]>C(#N)C.O1CCCC1>[C:41]([NH:48][C:49]1([CH2:52][O:9][CH:3]2[C:4]([CH3:8])([CH3:7])[CH2:5][CH2:6][C:2]2([CH3:10])[CH3:1])[CH2:51][CH2:50]1)([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 24758Sodium hydrideHCID 5516962,2,5,5-Tetramethylcyclopentan-1-olHCID 20092326Ethoxyethane;1,4,7,10,13,16-hexaoxacyclooctadecaneHCID 20165745N-Boc-1-amino-1-hydroxymethylcyclopropane mesylate

Produkt 1

HCID 20165730N-Boc-O-(2,2,5,5-tetramethyl-1-cyclopentyl)-1-amino-1-hydroxymethylcyclopropane

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 6342AcetonitrileLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

2,2,5,5-Tetramethyl-1-cyclopentanol is added to a dry flask under argon at 0° C. Dry tetrahydrofuran is added with a syringe. Sodium hydride (60% dispersion in oil) is added quickly in one portion and the contents of the flask are stirred for one hour at room temperature. A 10 mM solution of 18-crown-6- ether in acetonitrile is added with a syringe and the flask cooled to 0° C. A tetrahydrofuran solution of N-Boc-1-amino-1-hydroxymethylcyclopropane mesylate is added with vigorous stirring over a 10 minute period. After completion of the reaction, as judged by thin layer chromatography, it is quenched with dimethyl sulfate, poured into saturated ammonium chloride and extracted with ethyl acetate. The organic layer is dried over MgSO4 and evaporated to yield N-Boc-O-(2,2,5,5-tetramethyl-1-cyclopentyl)-1-amino-1-hydroxymethylcyclopropane.

Aufarbeitung

  1. temperaturethe flask cooled to 0° C
  2. stirringwith vigorous stirring over a 10 minute period
  3. customAfter completion of the reaction
  4. customis quenched with dimethyl sulfate
  5. additionpoured into saturated ammonium chloride
  6. extractionextracted with ethyl acetate
  7. dry with materialThe organic layer is dried over MgSO4
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-fc2ab26bae4748f5ac9058042d4d93d0
Quelldatensatz
uspto-grants-1986_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04622418

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion