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

HRID 1167680Notes

Reaction equation

HRID 1167680 reaction equation
[C-]#N.[K+].[C:4]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]1)=[O:10])([CH3:7])([CH3:6])[CH3:5].[C:18](=[O:21])([O-])[O-].[NH4+:22].[NH4+:23].Cl.C[CH2:26][OH:27].O>>[O:27]=[C:26]1[NH:23][C:18](=[O:21])[C:14]2([CH2:15][CH2:16][N:11]([C:9]([O:8][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:10])[CH2:12][CH2:13]2)[NH:22]1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 9032Potassium CyanideHCID 517111Ammonium CarbonateHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 19096565Water ethanol

Product 1

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

Conditions

Temperature
60 °C

Procedure

2.12 g (32.6 mmol) of potassium cyanide are added to a solution of 5 g (25.1 mmol) of N tert-butoxycarbonyl-4-piperidone (34.1) and 24.01 g (250 mmol) of ammonium carbonate in 80 ml of EtOH/water=1/1 and the mixture is left to stir at 60° C. for 5 h. The pH is subsequently adjusted to 6.3 by adding 6N HCl and the mixture is stirred at 60° C. for a further 1.5 h. The precipitate is filtered off with suction and dried under high vacuum. 3.43 g of (34.2) are obtained as a colorless solid. A further 1.0 g of (34.2) is obtained by extracting the filtrate with dichloromethane, drying the organic phase over sodium sulfate, filtering and removing the solvent in vacuo. Total yield of (34.2): 4.43 g (66%) of colorless solid.

Workup

  1. waitthe mixture is left
  2. stirringthe mixture is stirred at 60° C. for a further 1.5 h
  3. filtrationThe precipitate is filtered off with suction
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-bacc7c5fae734cbca72a2d57af95e9ce
Source dataset
uspto-grants-2003_09
Patent number
US06620820B2

Reaction notes

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