1-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acid → Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

HRID 23958

Reaktionsgleichung

Reaktionsgleichung von HRID 23958
[C:1]([N:8]1[CH2:16][CH2:15][CH:11]([C:12](O)=[O:13])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].B.C1COCC1>C1COCC1>[C:1]([N:8]1[CH2:16][CH2:15][CH:11]([CH2:12][OH:13])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Komponenten

4

Edukt 2

HCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 2723981Borane;tetrahydrofuran

Produkt 1

HCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1-Boc-isonipecotic acid (10.0 g, 214 mmol) was dissolved in THF (400 mL) and cooled to 0° C. A solution of BH3-THF (180 mL, 1 N in THF, 180 mmol) was added slowly. The mixture stirred for 1 h at 0° C. and was allowed to warm to room temperature for 12 h. The mixture was carefully quenched with water and diluted with ethyl acetate. The water layer was extracted with ethyl acetate. The organic layers were combined, washed with brine, dried (Na2SO4), filtered and concentrated to provide l-Boc-piperidine-4-methanol (7.98 g, 85%) as a white solid.

Aufarbeitung

  1. temperatureto warm to room temperature for 12 h
  2. customThe mixture was carefully quenched with water
  3. additiondiluted with ethyl acetate
  4. extractionThe water layer was extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-69907c3ae526490195aad8c034f65fdb
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855715B1

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