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

HRID 1507672Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

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)+

Workup

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

Sources & evidence

ORD record: ord-77d3f67b18c24bbbb40cb6af408abb5a
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221819B2

Reaction notes

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