Lauric Acid → 1-oxododecyl-3-(O-tert-butyldimethylsilyoxy)piperidine

HRID 2395713Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2395713
[C:1]([OH:14])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C(Cl)(=O)C(Cl)=O.[Si:21]([O:28][CH:29]1[CH2:34][CH2:33][CH2:32][NH:31][CH2:30]1)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22].C(N(CC)CC)C>C(Cl)Cl.CN(C)C=O>[O:14]=[C:1]([N:31]1[CH2:32][CH2:33][CH2:34][CH:29]([O:28][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:22])[CH3:23])[CH2:30]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Komponenten

7

Edukt 4

HCID 3893Lauric AcidHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 223524143-((Tert-butyldimethylsilyl)oxy)piperidine

Produkt 1

HCID 189895461-oxododecyl-3-(O-tert-butyldimethylsilyoxy)piperidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Dissolve lauric acid (0.77 g) in methylene chloride (50mL) and cool to 0° C. Add oxalyl chloride (0.37 mL) and dimethylformamide (3 drops). Allow to warm to room temperature and stir for 1 hour. Add, by dropwise addition, to a solution of 3-(O-tert-butyldimethylsilyloxy)piperidine (0.76 g, 3.5 mmol) and triethylamine (1 mL) in methylene chloride (20 mL). Stir overnight. Dilute with methylene chloride (50 mL) and separate the organic phase. Wash twice with 10% sodium hydroxide, once with 10% hydrochloric acid, and once with saturated sodium hydrogen carbonate and once with brine. Dry (Na2SO4) and evaporate the solvent in vacuo to give 1-oxododecyl-3-(O-tert-butyldimethylsilyoxy)piperidine.

Aufarbeitung

  1. temperatureAllow to warm to room temperature
  2. stirringStir overnight
  3. customseparate the organic phase
  4. washWash twice with 10% sodium hydroxide, once with 10% hydrochloric acid
  5. dry with materialDry (Na2SO4)
  6. customevaporate the solvent in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-09da1355281f47208f3af32d81f56483
Quelldatensatz
uspto-grants-1996_02
Patentnummer
US05489600

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