Dimethyl Sulfoxide → tert-Butyl 4-acetyl-4-(2-(tert-butyldimethylsilyloxy)eth-1-yl)piperidine-1-carboxylate

HRID 8770

Reaktionsgleichung

Reaktionsgleichung von HRID 8770
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH:12]([C:14]1([CH2:27][CH2:28][O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1)[CH3:13].C(N(CC)CC)C>C(Cl)Cl.O>[C:12]([C:14]1([CH2:27][CH2:28][O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:25])([CH3:26])[CH3:24])=[O:21])[CH2:16][CH2:15]1)(=[O:11])[CH3:13]

Komponenten

7

Edukt 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 21983937tert-Butyl 4-(1-hydroxyeth-1-yl)-4-(2-(tert-butyldimethylsilyloxy)eth-1-yl)piperidine-1-carboxylate

Produkt 1

HCID 21983972tert-Butyl 4-acetyl-4-(2-(tert-butyldimethylsilyloxy)eth-1-yl)piperidine-1-carboxylateAusbeute 68,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of oxalyl chloride (3.0 mL, 34 mmol) in methylene chloride (400 mL) at −70° C. was added DMSO (4.8 mL, 68 mmol) over 5 min. After 15 min, a solution of tert-butyl 4-(1-hydroxyeth-1-yl)-4-(2-(tert-butyldimethylsilyloxy)eth-1-yl)piperidine-1-carboxylate (6.6 g, 17 mmol) in methylene chloride (125 mL) was slowly added over 15 min. After 1 h, triethylamine (19 mL, 136 mmol) was added and the reaction was allowed to warm to room temperature for 1 h. The mixture was poured into water and extracted three times with methylene chloride. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (10% ethyl acetate in hexanes) to afford the title product (4.5 g).

Aufarbeitung

  1. waitAfter 1 h
  2. extractionextracted three times with methylene chloride
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (10% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-8f33fd77764b4fe7a6059f8325c13e1b
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091211B2

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