Sodium Bicarbonate → Tert-butyl 2-hydroxy-7-azaspiro[3.5]nonane-7-carboxylate

HRID 587118Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 587118
[O:1]=[C:2]1[CH2:5][C:4]2([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)[CH2:3]1.[BH4-].[Na+].C([O-])(O)=O.[Na+]>CO>[OH:1][CH:2]1[CH2:5][C:4]2([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)[CH2:3]1

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 11195798Tert-butyl 2-oxo-7-azaspiro[3.5]nonane-7-carboxylate

Produkt 1

HCID 9834677Tert-butyl 2-hydroxy-7-azaspiro[3.5]nonane-7-carboxylateAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 2-oxo-7-azaspiro[3.5]nonane-7-carboxylate (600 mg, 2.5 mmol, 1.0 equiv) in MeOH (6.0 mL) was added sodium borohydride (190 mg, 5.0 mmol, 2.0 equiv) in portions at 0° C. under nitrogen. The mixture was stirred at room temperature for 2.0 hrs. The solution was concentrated by evaporator to give the white solid. Saturated NaHCO3 solution (40 mL) was added. The aqueous phase was extracted with DCM (4×30 mL). The combined organic phase was dried over anhydrous Na2SO4, concentrated to give the crude which was purified by CombiFlash (24 g silica gel column, EtOAc/Hexane=0-60%) to afford 334 mg (yield 57%) of tert-butyl 2-hydroxy-7-azaspiro[3.5]nonane-7-carboxylate as a white solid.

Aufarbeitung

  1. concentrationThe solution was concentrated by evaporator
  2. customto give the white solid
  3. extractionThe aqueous phase was extracted with DCM (4×30 mL)
  4. dry with materialThe combined organic phase was dried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customto give the crude which
  7. customwas purified by CombiFlash (24 g silica gel column, EtOAc/Hexane=0-60%)

Quellen und Nachweise

ORD-Eintrag
ord-f8c888775fca44afa279ba566c711b7b
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09226923B2

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