Methanol → Benzyl 5-hydroxy-2-methylpiperidine-1-carboxylate

HRID 1749369Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1749369
C1COCC1.CO.[Li+].[BH4-].[CH3:10][CH:11]1[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][N:12]1[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]>CC(C)=O>[CH2:21]([O:20][C:18]([N:12]1[CH2:13][CH:14]([OH:17])[CH2:15][CH2:16][CH:11]1[CH3:10])=[O:19])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 71305938Benzyl 2-methyl-5-oxopiperidine-1-carboxylate

Produkt 1

HCID 71305932Benzyl 5-hydroxy-2-methylpiperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a solution of THF (200 mL) and MeOH (11 mL) was added LiBH4 (2 M, 89 mL, 0.18 mol). Some gas evolution and small exotherm were observed. The reaction was aged at room temperature for 30 min before being cooled to −10° C. with an acetone:ice bath. ±benzyl 2-methyl-5-oxopiperidine-1-carboxylate (22.0 g, 0.089 mol) was then added dropwise, keeping the temperature below −5° C. The reaction was then aged at −10° C. for 30 min. The reaction was quenched by adding half-saturated, aqueous NaHCO3, then extracted with EtOAc. The layers were separated and the organics dried with MgSO4. The organics were concentrated to give the titled compound as a crude, colorless oil.

Aufarbeitung

  1. customthe temperature below −5° C
  2. waitThe reaction was then aged at −10° C. for 30 min
  3. customThe reaction was quenched
  4. additionby adding half-saturated
  5. extractionaqueous NaHCO3, then extracted with EtOAc
  6. customThe layers were separated
  7. dry with materialthe organics dried with MgSO4
  8. concentrationThe organics were concentrated

Quellen und Nachweise

ORD-Eintrag
ord-522d2eeaab7c42bca6839abc49fd9316
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156819B2

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