Potassium Cyanide → Tert-butyl 2,4-dioxo-1,3,8-triazaspiro[4.5]decane-8-carboxylate

HRID 1241461Notes

Reaction equation

O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[C:15](=[O:18])([O-])[O-].[NH4+:19].[NH4+:20].[C-]#N.[K+].[CH2:24]([OH:26])C.O>>[O:26]=[C:24]1[NH:20][C:15](=[O:18])[C:2]2([CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]2)[NH:19]1

Participants

Reactant 4

HCID 9032Potassium Cyanide

HCID 517111Ammonium Carbonate

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

HCID 19096565Water ethanol

Product 1

HCID 3629994Tert-butyl 2,4-dioxo-1,3,8-triazaspiro[4.5]decane-8-carboxylateYield 53%

Conditions

Temperature: 60 °C

Procedure

A solution of tert-butyl 4-oxopiperidine-1-carboxylate (2.15 g, 10.8 mmol), in 1:1 ethanol/H2O (24 mL), was treated with ammonium carbonate (1.95 g, 21.2 mmol) followed by potassium cyanide (1.30 g, 20 mmol). The mixture was stirred at 60° C. for 2 hours, cooled to room temperature, filtered, and washed sequentially with water, ethanol, and diethyl ether to provide the desired product as a white crystalline solid (1.54 g, 53% yield). 1H NMR (300 MHz, DMSO-d6) δ 10.71 (1H, s), 8.51 (1H, s), 3.80 (2H, d, J=13.5 Hz), 3.09 (2H, br s), 1.66 (2H, td, J=12.2, 4.3 Hz), 1.53–1.46 (2H, m), 1.39 (9H, s). LCMS (2M+H) calcd. for C12H20N3O4: 539.28; found 539.41.

Workup

temperaturecooled to room temperature
filtrationfiltered
washwashed sequentially with water, ethanol, and diethyl ether

Sources & evidence

ORD record: ord-a82bd489a9c74c0f9189d1a2702a1549
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115601B2

Reaction notes

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