Propanal → tert-Butyl 4-(3-hydroxy-1-oxopent-1-yl)-4-methoxypiperidine-1-carboxylate

HRID 8756

Reaktionsgleichung

Reaktionsgleichung von HRID 8756
[C:1]([C:4]1([O:17][CH3:18])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C(NC(C)C)(C)C.[Li].[CH:27](=[O:30])[CH2:28][CH3:29].[Cl-].[NH4+]>O1CCCC1>[OH:30][CH:27]([CH2:28][CH3:29])[CH2:2][C:1]([C:4]1([O:17][CH3:18])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])[CH2:6][CH2:5]1)=[O:3]

Komponenten

6

Edukt 4

HCID 527PropanalHCID 25517Ammonium ChlorideHCID 21983927Tert-butyl 4-acetyl-4-methoxypiperidine-1-carboxylateHCID 45051747Lithium diisopropylamine

Produkt 1

HCID 21984004tert-Butyl 4-(3-hydroxy-1-oxopent-1-yl)-4-methoxypiperidine-1-carboxylateAusbeute 55,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 4-acetyl-4-methoxypiperidine-1-carboxylate (0.589 g, 2.29 mmol) from Step A in tetrahydrofuran (20 mL) at −78° C. was added lithium diisopropylamine (0.650 mL, 0.974 mmol) followed by propionaldehyde (0.266 g, 0.330 mL, 4.58 mmol). After 5 min, the reaction mixture was poured into saturated ammonium chloride, and extracted three times with diethyl ether. The organic layers were combined, washed with saturated sodium chloride solution, dried over sodium sulfite, filtered, and concentrated. The residue was purified by flash chromatography eluting with 40% ethyl acetate/hexanes to afford the title compound (0.404 g). MS/EI (acetonitrile/water): m/z 216.1 (M+1−BOC) retention time=2.69 min.

Aufarbeitung

  1. extractionextracted three times with diethyl ether
  2. washwashed with saturated sodium chloride solution
  3. dry with materialdried over sodium sulfite
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography
  7. washeluting with 40% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-b89820f3efd14138aa3a6cb136df92cc
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091211B2

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