Ammonium Chloride → HCID 90791180, Verbindung

HRID 1743260

Reaktionsgleichung

Reaktionsgleichung von HRID 1743260
[O:1]=[C:2]1[O:7][C@H:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C@H:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:4]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:3]1.C1OCCOCCOCCOCCOC1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].I[CH:53]1[CH2:58][CH2:57][N:56]([C:59]([O:61][CH2:62][CH2:63][Si:64]([CH3:67])([CH3:66])[CH3:65])=[O:60])[CH2:55][CH2:54]1.[Cl-].[NH4+]>C1COCC1>[O:1]=[C:2]1[O:7][C@@H:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C@@H:5]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:4]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C@@H:3]1[CH:53]1[CH2:54][CH2:55][N:56]([C:59]([O:61][CH2:62][CH2:63][Si:64]([CH3:67])([CH3:66])[CH3:65])=[O:60])[CH2:57][CH2:58]1

Komponenten

7

Edukt 5

HCID 25517Ammonium ChlorideHCID 3633615-Crown-5HCID 981230tert-butyl (2R,3S)-6-oxo-2,3-diphenylmorpholine-4-carboxylateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 222384082-Trimethylsilanylethyl 4-iodopiperidine-1-carboxylate

Produkt 1

HCID 90791180HCID 90791180, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

4 g of tert-butyl (5S,6R)-2-oxo-5,6-diphenylmorpholine-4-carboxylate were dissolved in 50 ml of THF. 9 ml of 15-crown-5 were added, and the mixture was cooled to −78° C. Then 6.8 ml of a 2 M solution of NaHMDS in THF were added dropwise. The mixture was stirred for 10 min and then 8 g of 2-trimethylsilanylethyl 4-iodopiperidine-1-carboxylate were added dropwise. The mixture was allowed to warm to 0° C. over the course of 6 h, and then the reaction was stopped by adding 200 ml of saturated ammonium chloride solution. The aqueous phase was extracted 3 times with 150 ml of ethyl acetate each time, and the combined organic phases were dried with MgSO4. The solvents were removed in vacuo, and the residue was chromatographed on silica gel.

Aufarbeitung

  1. temperatureto warm to 0° C. over the course of 6 h
  2. extractionThe aqueous phase was extracted 3 times with 150 ml of ethyl acetate each time
  3. dry with materialthe combined organic phases were dried with MgSO4
  4. customThe solvents were removed in vacuo
  5. customthe residue was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-3e41b89821224680bb8e0715a9e0af01
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07008957B2

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