tert-Butyl 3-oxo-8-azabicyclo(3.2.1)octane-8-carboxylate → tert-Butyl 3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate

HRID 446711Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 446711
[C:1]([O:5][C:6]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][C:11](=[O:16])[CH2:12]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>C(O)C.ClCCl>[C:1]([O:5][C:6]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][CH:11]([OH:16])[CH2:12]2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 2

HCID 2794767tert-Butyl 3-oxo-8-azabicyclo(3.2.1)octane-8-carboxylate2×HCID 4311764Sodium borohydride

Produkt 1

HCID 21187725tert-Butyl 3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylateAusbeute 93,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3-Oxo-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (Compound 1009, 8 g, 35.5 mmol) was dissolved in 100 mL of ethanol. Sodium borohydride (2 g, 53.5 mmol) was added to the solution portionwise at room temperature. After stirring for 3 hours, the reaction was evaporated in vacuo to give clear viscous oil. The oil was dissolved in dichloromethane, washed with water and brine, dried over anhydrous sodium sulfate, filtered and evaporated to afford 7.55 g of 3-hydroxy-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (Compound 1010) as a white crystalline solid; 1H NMR (300 MHz, DMSO-d6): δ 4.23 (dd, J=2.7, 4.6 Hz, 1H), 4.18-4.06 (m, 2H), 2.17-2.06 (m, 1H), 1.99-1.91 (m, 3H), 1.72-1.50 (m, 5H), 1.47 (s, 9H).

Aufarbeitung

  1. customthe reaction was evaporated in vacuo
  2. customto give clear viscous oil
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-606c2d2fad3543d2b6d6a78e4aec908a
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481524B2

Notizen zur Reaktion

Wird geladen…