Ammonium Chloride → acrylic acid (S)-6-[4-[2-(hydroxydinaphthalen-2-ylmethyl)pyrrolidine-1-carbonyl]phenoxy]hexyl ester

HRID 413608Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 413608
S(Cl)(C)(=O)=O.[C:6]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=O)=[CH:20][CH:19]=1)(=[O:9])[CH:7]=[CH2:8].[CH:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][C:28]=1[C:37]([C:44]1[CH:53]=[CH:52][C:51]2[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=2)[CH:45]=1)([C@@H:39]1[CH2:43][CH2:42][CH2:41][NH:40]1)[OH:38].[NH4+].[Cl-]>C1COCC1.C(N(CC)CC)C>[OH:38][C:37]([C:28]1[CH:29]=[CH:30][C:31]2[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:27]=1)([C:44]1[CH:53]=[CH:52][C:51]2[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=2)[CH:45]=1)[C@@H:39]1[CH2:43][CH2:42][CH2:41][N:40]1[C:22]([C:21]1[CH:20]=[CH:19][C:18]([O:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][O:10][C:6](=[O:9])[CH:7]=[CH2:8])=[CH:26][CH:25]=1)=[O:24]

Komponenten

7

Edukt 4

HCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 2733810(S)-Di(naphthalen-2-yl)(pyrrolidin-2-yl)methanolHCID 37135654-((6-(Acryloyloxy)hexyl)oxy)benzoic acid

Produkt 1

HCID 59064084acrylic acid (S)-6-[4-[2-(hydroxydinaphthalen-2-ylmethyl)pyrrolidine-1-carbonyl]phenoxy]hexyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel3×HCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

A solution of mesyl chloride (0.1 ml) in 1 ml of dry THF is added dropwise under argon over a period of 15 minutes to a cooled (−20° C.) solution of 4-(6-acryloyloxyhexyloxy)benzoic acid (0.38 g) and triethylamine (0.52 ml) in 10 ml of dry THF. The obtained reaction mixture is stirred for 60 min at −20° C. then treated with a solution of (S)-dinaphthalen-2-ylpyrrolidin-2-ylmethanol (0.46 g) in 5 ml of dry THF and further stirred at −20° C. for 2 h. The reaction mixture is then allowed to warm to room temperature, and stirring is continued overnight. The reaction mixture is then poured into 40 ml of saturated NH4Cl solution and extracted with 4×40 ml of diethyl ether and 20 ml of dichloromethane. The combined organic extracts are washed with saturated NaCl solution (2×80 ml), dried over MgSO4, filtered and evaporated to give a brownish residue. This was purified by chromatography over a short silica column (CH2Cl2 / Et2O : 19 / 1 ) to give acrylic acid (S)-6-[4-[2-(hydroxydinaphthalen-2-ylmethyl)pyrrolidine-1-carbonyl]phenoxy]hexyl ester as a white crystalline material. Yield 0.51 g.

Aufarbeitung

  1. customThe obtained reaction mixture
  2. stirringfurther stirred at −20° C. for 2 h
  3. temperatureto warm to room temperature
  4. stirringstirring
  5. waitis continued overnight
  6. extractionextracted with 4×40 ml of diethyl ether and 20 ml of dichloromethane
  7. washThe combined organic extracts are washed with saturated NaCl solution (2×80 ml)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated
  11. customto give a brownish residue
  12. customThis was purified by chromatography over a short silica column (CH2Cl2 / Et2O : 19 / 1 )

Quellen und Nachweise

ORD-Eintrag
ord-fe11548d0b0b4033beeafd94165b0d1f
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06569356B1

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