Water → (1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)methanol

HRID 353337Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 353337
[C:1]1([CH2:7][N:8]2[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][CH:9]2Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].O>CO>[C:1]1([CH2:7][N:8]2[CH2:9][CH:10]=[C:11]([CH2:14][OH:15])[CH2:12][CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 22708810HCID 22708810, Verbindung

Produkt 1

HCID 11264156(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)methanolAusbeute 87,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

1-(Phenylmethyl)-4-(hydroxymethyl)-pyridinyl chloride(0.87 mol) was dissolved in methanol (2200 ml) and cooled to −20° C. Sodium borohydride (1.75 mol) was added portionwise under a nitrogen atmosphere. The reaction mixture was stirred for 30 minutes and water (200 ml) was added dropwise. The reaction mixture was partially evaporated, water was added and the reaction mixture was extracted with DCM. The organic layer was separated, dried, filtered and evaporated. The residue was purified over silica gel (eluent: DCM), yielding 155 g of 1,2,3,6-tetrahydro-1-(phenylmethyl)-4-pyridinemethanol.

Aufarbeitung

  1. customThe reaction mixture was partially evaporated
  2. additionwater was added
  3. extractionthe reaction mixture was extracted with DCM
  4. customThe organic layer was separated
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified over silica gel (eluent: DCM)

Quellen und Nachweise

ORD-Eintrag
ord-6c95b6718aa342dc8b0c2d9f99cce244
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06750349B2

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