Ethyl Acrylate → HCID 12936817, compound

HRID 2226842Notes

Reaction equation

HRID 2226842 reaction equation
[N+:1]([CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)([O-:3])=[O:2].[C:10]([O:14][CH2:15][CH3:16])(=[O:13])[CH:11]=[CH2:12]>C(O)(C)(C)C>[N+:1]([C:4]1([CH2:12][CH2:11][C:10]([O:14][CH2:15][CH3:16])=[O:13])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 8821Ethyl AcrylateHCID 14285Nitrocyclohexane

Product 1

HCID 12936817HCID 12936817, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

99.5 g of nitrocyclohexane was dissolved in 40 ml of t-butanol, and 83.4 ml of ethyl acrylate was added thereto in the presence of 7 ml of 40% Triton B. The mixture was reacted at room temperature to give 153 g (yield: 87%) of 1-nitro-l-(2-ethoxycarbonylethyl)cyclohexane. Then, 20 g of this substance was dissolved in ethanol and 3.6 g of Raney nickel was added thereto. The mixture was strongly stirred in the presence of hydrogen gas (70 kg/cm2), and then the Raney nickel was removed. The reaction solution was refluxed under heating for 5 hours. Then, ethanol was distilled off to give 8.0 g (yield: 62%) of 1-aza-2-oxospiro[4.5]decane8.0 g of this substance was dissolved in 30 ml of THF, and 3.6 g of LiAlH4 was added thereto. The mixture was reacted at room temperature for 15 hours to give 7.4 g (yield: 83%) of 1-azaspiro[4.5]decane.

Workup

  1. customThe mixture was reacted at room temperature

Sources & evidence

ORD record
ord-a9b54eac663b4d76a9d63a97a57b3149
Source dataset
uspto-grants-1994_09
Patent number
US05350743

Reaction notes

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