1,1-Dichloroethane → HCID 58808179, Verbindung

HRID 548941

Reaktionsgleichung

Reaktionsgleichung von HRID 548941
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2([CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[CH:20](Cl)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>O>[OH-:5].[NH4+:8].[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2([CH2:18][CH2:17][N:16]([CH3:20])[CH2:15][CH2:14]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

7

Edukt 4

HCID 63651,1-DichloroethaneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 15296367tert-Butyl 3,9-diazaspiro[5.5]undecane-3-carboxylate

Produkt 2

HCID 14923Ammonium HydroxideAusbeute 1 %HCID 58808179HCID 58808179, VerbindungAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To an ice cooled solution of 3,9-diaza-spiro[5.5]undecane-3-carboxylic acid tert-butyl ester (1.55 g, 6 mmol) in dichloroethane (50 mL) formaldehyde (0.68 mL, 9 mmol) was added and stirred for 1 h at 0° C. Sodium triacetoxyborohydride (2.54 g, 12 mmol) was added and the reaction stirred at room temperature over night. Aqueous sodium hydrogencarbonate (sat. 50 mL) and water (50 mL) were added and the aqueous phase extracted five times with dichloromethane. The combined organic phase was washed with brine, dried (sodium sulfate), filtered and evaporated. Flash chromatography (dichloromethane/methanol 9:1 with 1% ammonium hydroxide) gave 435 mg (27%) 9-methyl-3,9-diaza-spiro[5.5]undecane-3-carboxylic acid tert-butyl ester.

Aufarbeitung

  1. stirringthe reaction stirred at room temperature over night
  2. extractionthe aqueous phase extracted five times with dichloromethane
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-902bcdbedc3347739f3f0bce9abaae64
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07943630B2

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