Water → (7R)-benzyl 2,4-dioxo-1,3-diazaspiro[4.4]nonane-7-carboxylate

HRID 331102Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 331102
O=[C:2]1[CH2:6][CH2:5][C@@H:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:3]1.[C-:17]#[N:18].[Na+].[C:20](=[O:23])([O-])[O-].[NH4+:24].[NH4+].[OH2:26]>C(O)C>[O:26]=[C:17]1[NH:24][C:20](=[O:23])[C:2]2([CH2:6][CH2:5][C@@H:4]([C:7]([O:9][CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:8])[CH2:3]2)[NH:18]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8929Sodium CyanideHCID 517111Ammonium CarbonateHCID 86668857(R)-benzyl 3-oxocyclopentanecarboxylate

Produkt 1

HCID 68179167(7R)-benzyl 2,4-dioxo-1,3-diazaspiro[4.4]nonane-7-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To (R)-benzyl 3-oxocyclopentanecarboxylate (0.5 g, 2.291 mmol) in ethanol (5 mL) were sequentially added sodium cyanide (0.281 g, 5.73 mmol), ammonium carbonate (2.86 g, 29.8 mmol) and water (5.00 mL) at room temperature. The contents were heated at 70° C. (oil bath temp.) for 3 hours. The reaction mixture was kept at room temperature for 10 min. Solid separates out. The solid was filtered and washed with water (3×10 mL). The solid was dried overnight under vacuum (155 mg, 0.538 mmol, 23.5%) and used as such for the subsequent step without further purification. MS (ESI) m/z 289.16 (M+H)+

Aufarbeitung

  1. customat room temperature
  2. filtrationThe solid was filtered
  3. washwashed with water (3×10 mL)
  4. customThe solid was dried overnight under vacuum (155 mg, 0.538 mmol, 23.5%)
  5. customwithout further purification

Quellen und Nachweise

ORD-Eintrag
ord-24fdb3dcca614906b838a33b7cfb166d
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877749B2

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