Triethylamine → tert-Butyl (1-(2-hydroxypropyl)piperidin-4-yl)carbamate

HRID 255389Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 255389
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:3][CH2:2]1.Br[CH2:16][CH:17]([OH:19])[CH3:18].BrC(C)CO.C(N(CC)CC)C>C(#N)C>[OH:19][CH:17]([CH3:18])[CH2:16][N:1]1[CH2:2][CH2:3][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[CH2:5][CH2:6]1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 117132-Bromopropan-1-olHCID 297401-Bromo-2-propanolHCID 7238334-(N-Boc-amino)piperidine

Produkt 1

HCID 56973353tert-Butyl (1-(2-hydroxypropyl)piperidin-4-yl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

tert-Butyl piperidin-4-ylcarbamate (2.0 g, 10.0 mmol), 1-bromopropan-2-ol (2.8 g, 20.0 mmol, commercial product which also contained 30% of the regioisomer 2-bromopropan-1-ol), triethylamine (4.2 mL, 30.0 mmol), and acetonitrile (15 mL) were combined in a microwave vial and heated to 70° C. for 4 hours. The reaction mixture was concentrated to dryness. The crude product was partitioned between ethyl acetate/water. The aqueous phase was re-extracted 2× with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered, and concentrated to dryness. The product was purified by flash chromatography on silica gel eluting with a gradient of 20-30% methanol in dichloromethane to give 1.7 g of the desired product as an oil.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customThe crude product was partitioned between ethyl acetate/water
  3. extractionThe aqueous phase was re-extracted 2× with ethyl acetate
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe product was purified by flash chromatography on silica gel eluting with a gradient of 20-30% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-3e11c137c99a4ccb942b1c74a5e055d9
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07875715B2

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