Triethylamine → tert-Butyl 6-oxo-1,7-diazaspiro[4.4]nonane-1-carboxylate

HRID 1850638Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1850638
Cl.[NH:2]1[C:6]2([CH2:10][CH2:9][NH:8][C:7]2=[O:11])[CH2:5][CH2:4][CH2:3]1.[C:12]([O:16][C:17](OC([O-])=O)=[O:18])([CH3:15])([CH3:14])[CH3:13].C(N(CC)CC)C>ClCCl.O>[C:12]([O:16][C:17]([N:2]1[C:6]2([CH2:10][CH2:9][NH:8][C:7]2=[O:11])[CH2:5][CH2:4][CH2:3]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 22064466Tert-butyldicarbonateHCID 866866531,7-Diazaspiro(4.4)nonan-6-one hydrochloride

Produkt 1

HCID 49760540tert-Butyl 6-oxo-1,7-diazaspiro[4.4]nonane-1-carboxylateAusbeute 100,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1,7-diazaspiro[4,4]nonan-6-one hydrochloride (0.98 g, 5.4 mmol) in dichloromethane were added tert-butyldicarbonate (1.41 g, 6.48 mmol) and triethylamine (1.3 g, 13.5 mmol). The resulting solution was stirred overnight at room temperature. The solution was diluted with water and extracted with dichloromethane. The organic phase was separated, dried, filtered and concentrated to afford 6-oxo-1,7-diaza-spiro[4,4]nonan-1-carboxylic acid tert-butyl ester product as white powder (1.3 g) in 100% yield and used directly without further purification. 1H NMR (400 MHz, CD2Cl2) δ 6.13-5.74 (br, 1H), 3.59-3.20 (m, 4H), 2.75-2.49 (m, 1H), 2.16-1.76 (m, 5H), 1.43 (s, 3H), 1.42 (s, 6H). MS m/z 241.2 (M+H)+

Aufarbeitung

  1. extractionextracted with dichloromethane
  2. customThe organic phase was separated
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-1389c5024e194f31946780253668b876
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957074B2

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