Sodium borohydride → tert-Butyl 4-hydroxy-3-(hydroxymethyl)piperidine-1-carboxylate

HRID 1972065Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1972065
C([O:3][C:4]([CH:6]1[C:11](=[O:12])[CH2:10][CH2:9][N:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:7]1)=O)C.[BH4-].[Na+]>CO>[C:16]([O:15][C:13]([N:8]1[CH2:9][CH2:10][CH:11]([OH:12])[CH:6]([CH2:4][OH:3])[CH2:7]1)=[O:14])([CH3:19])([CH3:18])[CH3:17]

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 64208761-(1,1-Dimethylethyl) 3-ethyl 4-oxo-1,3-piperidinedicarboxylate

Produkt 1

HCID 66717856tert-Butyl 4-hydroxy-3-(hydroxymethyl)piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 4-oxo-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (51.59 mmol, 14 g) in methanol (300 mL) was added sodium borohydride (12 g) in 12 portions over 30 min. The reaction mixture was stirred for additional 30 min, and the volatiles were removed under reduced pressure. To the residue was added saturated ammonium chloride (300 mL). The mixture was extracted with ethyl acetate (300 mL), and the organic layer was dried and concentrated under reduced pressure. The residue was purified on a flash silica gel column eluting with ethyl acetate to provide 4-hydroxy-3-hydroxymethyl-piperidine-1-carboxylic acid tert-butyl ester.

Aufarbeitung

  1. customthe volatiles were removed under reduced pressure
  2. additionTo the residue was added saturated ammonium chloride (300 mL)
  3. extractionThe mixture was extracted with ethyl acetate (300 mL)
  4. customthe organic layer was dried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified on a flash silica gel column
  7. washeluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-190d39cb5f774c09bf18d344fd74da0e
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08431575B2

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