Sodium Hydroxide → (S)-(1-Benzyl-3-methylpiperidin-3-yl)methanol

HRID 453818Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 453818
C([O:3][C:4]([C@@:6]1([CH3:19])[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:7]1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1>[CH2:12]([N:8]1[CH2:9][CH2:10][CH2:11][C@@:6]([CH2:4][OH:3])([CH3:19])[CH2:7]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 66727374(S)-1-Benzyl-3-methylpiperidine-3-carboxylic acid ethyl ester

Produkt 1

HCID 66727443(S)-(1-Benzyl-3-methylpiperidin-3-yl)methanolAusbeute 93,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

(S)-1-Benzyl-3-methylpiperidine-3-carboxylic acid ethyl ester (1.64 g, 6.3 mmol) in dry THF (20 ml) was slowly added to a stirred suspension of LiAlH4 (0.71 g, 18.8 mmol) in dry THF (20 ml) under nitrogen atmosphere. After the addition the mixture was refluxed for 1.5 h. The solution was cooled with an ice bath, stirred vigorously and 2.5 M NaOH was added carefully drop by drop until no reaction occurred and a white precipitate was formed. The solvent was decanted and the solid washed with EtOAc (2×20 ml). The combined organic phases were dried, filtered and evaporated to dryness to give 1.29 g of the alcohol product as a white powder.

Aufarbeitung

  1. additionAfter the addition the mixture
  2. temperaturewas refluxed for 1.5 h
  3. temperatureThe solution was cooled with an ice bath
  4. customa white precipitate was formed
  5. customThe solvent was decanted
  6. washthe solid washed with EtOAc (2×20 ml)
  7. customThe combined organic phases were dried
  8. filtrationfiltered
  9. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-b437037f21a144909dde80c77c1fe130
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492549B2

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