Ethanol → tert-butyl 2,4-dioxo-1,3,7-triazaspiro[4.5]decane-7-carboxylate

HRID 1639995Notes

Reaction equation

HRID 1639995 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.[C-]#N.[K+].[C:18](=[O:21])([O-])[O-].[NH4+:22].[NH4+:23].[CH2:24]([OH:26])C>O.C(OCC)(=O)C>[O:26]=[C:24]1[NH:23][C:18](=[O:21])[C:2]2([CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]2)[NH:22]1

Participants

7

Reactant 4

HCID 702EthanolHCID 9032Potassium CyanideHCID 517111Ammonium CarbonateHCID 2756825Tert-butyl 3-oxopiperidine-1-carboxylate

Product 1

HCID 42614218tert-butyl 2,4-dioxo-1,3,7-triazaspiro[4.5]decane-7-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of tert-butyl 3-oxopiperidine-1-carboxylate (0.20 g, 0.0010 mol), potassium cyanide (0.13 g, 0.0020 mol) and ammonium carbonate (0.77 g, 0.0080 mol) in ethanol (4.0 mL, 0.068 mol) and water (2.0 mL) was stirred at 70° C. for 4 h. The mixture was then diluted with ethyl acetate and washed with water, brine, dried and concentrated to give the desired product. LC-MS: 292.0 (M+Na)+.

Workup

  1. washwashed with water, brine
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-270b8f78de4545c7a1aad7ad8712852a
Source dataset
uspto-grants-2012_02
Patent number
US08110581B2

Reaction notes

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