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

HRID 627427Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 627427
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-d802bb7a4c34443bac9bd999e9c43860
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309252B2

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