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Sodium borohydride → Tert-butyl 9-(2-hydroxyethoxy)-3-azaspiro[5.5]undecane-3-carboxylate

HRID 1253721
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1253721
[BH4-].[Na+].[O:3]=[CH:4][CH2:5][O:6][CH:7]1[CH2:24][CH2:23][C:10]2([CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)[CH2:9][CH2:8]1>CO>[OH:3][CH2:4][CH2:5][O:6][CH:7]1[CH2:24][CH2:23][C:10]2([CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:14][CH2:15]2)[CH2:9][CH2:8]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 86645836tert-Butyl 9-(2-oxoethoxy)-3-azaspiro[5.5]undecane-3-carboxylate

Produkt 1

HCID 66700976Tert-butyl 9-(2-hydroxyethoxy)-3-azaspiro[5.5]undecane-3-carboxylateAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

NaBH4 (13.46 mmol, 2.0 eq.) was added portion wise to a stirred solution of tert-butyl 9-(2-oxoethoxy)-3-azaspiro[5.5]undecane-3-carboxylate (6.73 mmol, 1.0 eq.) in MeOH (65 ml) at 0° C. and the resulting reaction mixture was stirred at 25° C. for 16 h. The solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate (300 ml) and washed with water (200 ml) and brine (200 ml). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography eluting with 20% ethyl acetate in hexanes to give the desired product as a yellow sticky solid. Yield: 40%

Aufarbeitung

  1. customthe resulting reaction mixture
  2. customThe solvent was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate (300 ml)
  4. washwashed with water (200 ml) and brine (200 ml)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give the crude product
  8. customThe crude product was purified by silica gel column chromatography
  9. washeluting with 20% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-c0815286f4cd4c0baf17e42dd44103ce
Quelldatensatz
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08455475B2

Notizen zur Reaktion

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