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

Propyl mercaptan → N-(2-Propenyl)-cis-2-[4-(1,1-dimethylheptyl)-2-hydroxyphenyl]-4-piperidinol

HRID 371160
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 371160
C(S)CC.C([Li])CCC.[CH2:10]([N:13]1[CH2:18][CH2:17][C@H:16]([OH:19])[CH2:15][C@@H:14]1[C:20]1[CH:25]=[CH:24][C:23]([C:26]([CH3:34])([CH3:33])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:22][C:21]=1[O:35]CC1C=CC=CC=1)[CH:11]=[CH2:12].C([S-])CC.[Li+]>O1CCCC1.CCCCCC.CN(C)P(N(C)C)(N(C)C)=O>[CH2:10]([N:13]1[CH2:18][CH2:17][C@H:16]([OH:19])[CH2:15][C@@H:14]1[C:20]1[CH:25]=[CH:24][C:23]([C:26]([CH3:34])([CH3:33])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:22][C:21]=1[OH:35])[CH:11]=[CH2:12]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 7848Propyl mercaptanHCID 10909481Lithium propanethiolateHCID 70490735N-(2-Propenyl)-cis-2-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidinolHCID 178418339Butyllithium

Produkt 1

HCID 70491522N-(2-Propenyl)-cis-2-[4-(1,1-dimethylheptyl)-2-hydroxyphenyl]-4-piperidinolAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel

3
HCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittelHCID 12679HexamethylphosphoramideLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A solution of 6.8 ml (74.6 mmole) of propanethiol in 75 ml of tetrahydrofuran is degassed by three freeze-thaw cycles at 0.1 torr. The resultant solution is cooled to -78° C. and 28 ml of 2.5M n-butyllithium in hexane is added. The reaction is then allowed to warm to 25° C. and stirred 3 hours longer. The reaction is evaporated to dryness under high vacuum and the residue dissolved in 70 ml of degassed hexamethylphosphoramide. To a 25° C. degassed solution of 218 mg (0.486 mmole) of N-(2-propenyl)-cis-2-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidinol in 1 ml of hexamethylphosphoramide is added 2.2 ml of the above prepared solution of lithium propanethiolate. The reaction is stirred 30 minutes at 25° C. and 1.5 hour at 105° C. followed by cooling to 25° C. The reaction is quenched by addition to 30 ml water and the mixture extracted with 150 ml ethyl ether. The ether extract is washed twice with 30 ml water, once with 30 ml saturated sodium chloride, dried over magnesium sulfate and evaporated to an oil. The crude product is purified via column chromatography on 48 g of silica gel eluting in 8 ml fractions with ethyl ether to give (fractions 12-24) 101 mg (58%) of the title compound as an oil.

Aufarbeitung

  1. customThe reaction is evaporated to dryness under high vacuum
  2. dissolutionthe residue dissolved in 70 ml of degassed hexamethylphosphoramide
  3. stirringThe reaction is stirred 30 minutes at 25° C. and 1.5 hour at 105° C.
  4. temperatureby cooling to 25° C
  5. customThe reaction is quenched by addition to 30 ml water
  6. extractionthe mixture extracted with 150 ml ethyl ether
  7. extractionThe ether extract
  8. washis washed twice with 30 ml water, once with 30 ml saturated sodium chloride
  9. dry with materialdried over magnesium sulfate
  10. customevaporated to an oil
  11. customThe crude product is purified via column chromatography on 48 g of silica gel eluting in 8 ml fractions with ethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-ba3bf8426ac3456f956aad9db66b5dc6
Quelldatensatz
uspto-grants-1985_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04529732

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion