Formaldehyde → CID 59418223

HRID 1778467Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1778467
C(OC([N:11]1[CH:16]2[CH2:17][NH:18][CH2:19][CH:12]1[CH2:13][O:14][CH2:15]2)=O)C1C=CC=CC=1.[CH2:20]=O.[BH4-].[Na+]>CO>[CH3:20][N:18]1[CH2:17][CH:16]2[NH:11][CH:12]([CH2:13][O:14][CH2:15]2)[CH2:19]1

Komponenten

5

Edukt 3

HCID 712FormaldehydeHCID 4311764Sodium borohydrideHCID 673561213-Oxa-7,9-diaza-bicyclo[3.3.1]nonane-9-carboxylic acid benzyl ester

Produkt 1

HCID 59418223CID 59418223Ausbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 3-oxa-7,9-diaza-bicyclo[3.3.1]nonane-9-carboxylic acid benzyl ester (Compound X) (84 mg, 0.28 mmol) in MeOH (5 mL) was added paraformaldehyde (41 mg, 1.38 mmol) and NaBH4 (21 mg, 0.56 mmol). The reaction mixture was refluxed for 16 hours under argon atmosphere, and then quenched with sat. NaHCO3, then extracted with EtOAc (20 mL) three times. The combined organic layer was washed successively with sat. NH4Cl, NaHCO3 and brine, and then dried over Na2SO4. The solvent was concentrated under reduced pressure. The residue was dissolved in MeOH (20 mL). To the solution was added 10% Pd on carbon (20 mg). The mixture was stirred under one atmosphere pressure of hydrogen at room temperature. After the reaction was completed, the mixture was filtered and concentrated to give the crude 7-methyl-3-oxa-7,9-diaza-bicyclo[3.3.1]nonane (Compound Z) (32 mg, 81%) which was directly used for next step. MS: calc'd (MH+) 143, measured (MH+) 143.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 16 hours under argon atmosphere
  2. customquenched with sat. NaHCO3
  3. extractionextracted with EtOAc (20 mL) three times
  4. washThe combined organic layer was washed successively with sat. NH4Cl, NaHCO3 and brine
  5. dry with materialdried over Na2SO4
  6. concentrationThe solvent was concentrated under reduced pressure
  7. dissolutionThe residue was dissolved in MeOH (20 mL)
  8. additionTo the solution was added 10% Pd on carbon (20 mg)
  9. filtrationthe mixture was filtered
  10. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-1cad42920dd54738b5d1077e63a8ed92
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09266904B2

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