1,1-Dichloroethane → tert-Butyl 6-amino-2-azaspiro[3.3]heptane-2-carboxylate

HRID 336545

Reaktionsgleichung

Reaktionsgleichung von HRID 336545
[CH:1]([N:4](CC)C(C)C)(C)C.Cl[C:11]([O:13][C:14]1[CH:19]=CC([N+]([O-])=O)=C[CH:15]=1)=[O:12].O[CH2:24][C:25]1O[N:28]=[C:27]([C:30](OCC)=O)[CH:26]=1.Cl[CH:36](Cl)C>>[NH2:28][CH:27]1[CH2:26][C:25]2([CH2:24][N:4]([C:11]([O:13][C:14]([CH3:15])([CH3:19])[CH3:36])=[O:12])[CH2:1]2)[CH2:30]1

Komponenten

5

Edukt 4

HCID 63651,1-DichloroethaneHCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 8027233Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate

Produkt 1

HCID 46930560tert-Butyl 6-amino-2-azaspiro[3.3]heptane-2-carboxylate

Versuchsvorschrift

0.341 g (2.64 mmol) of N,N-diisopropylethylamine and 0.265 g (1.32 mmol) of 4-nitrophenyl chloroformate are added to a solution of 0.226 g (1.32 mmol) of ethyl 5-hydroxymethylisoxazole-3-carboxylate in 10 mL of dichloroethane. Stirring is continued at room temperature for hours and 0.280 g (1.32 mmol) of tert-butyl 6-amino-2-azaspiro[3.3]heptane-2-carboxylate, obtained in step 11.6., dissolved in 4 mL of dichloroethane, is then added. Stirring is continued at room temperature for 4 hours. Water is added to the reaction medium, the aqueous phase is separated out and extracted several times with dichloromethane, and the combined organic phases are washed with aqueous sodium hydroxide solution (1N) and then with saturated aqueous ammonium chloride solution. The resulting phase is dried over sodium sulfate and the filtrate is concentrated under reduced pressure. After evaporating off the solvent, the residue obtained is purified by chromatography on silica gel, eluting with a 98/2 mixture of dichloromethane and methanol.

Aufarbeitung

  1. waitis continued at room temperature for hours

Quellen und Nachweise

ORD-Eintrag
ord-315116fc95dc426e84a60580dd0a9a8c
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889702B2

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