Hydrochloric Acid → Benzyl ethyl(4-oxocyclohexyl)carbamate

HRID 2175545Notes

Reaction equation

HRID 2175545 reaction equation
[CH2:1]([N:3]([CH:14]1[CH2:23][CH2:22][C:17]2(OCC[O:18]2)[CH2:16][CH2:15]1)[C:4](=[O:13])[O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2].Cl>C(#N)C>[CH2:1]([N:3]([CH:14]1[CH2:23][CH2:22][C:17](=[O:18])[CH2:16][CH2:15]1)[C:4](=[O:13])[O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58562800Benzyl ethyl(1,4-dioxaspiro[4.5]decan-8-yl)carbamate

Product 1

HCID 58562517Benzyl ethyl(4-oxocyclohexyl)carbamate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Benzyl ethyl(1,4-dioxaspiro[4.5]decan-8-yl)carbamate (350 mg, 1.1 mmol) was dissolved in acetonitrile, treated with 6N HCl, and stirred at room temperature for 18 h. reaction mixture was concentrated in vacuo, treated with saturated NaHCO3 to pH 6. The solvents were removed under vacuum and the residue treated with saturated NaCl (2 mL) and extracted with 4:1 EtOAc/iPrOH (x4). The organic fractions were combined, filtered and evaporated to give the title compound.

Workup

  1. customreaction mixture
  2. concentrationwas concentrated in vacuo
  3. additiontreated with saturated NaHCO3 to pH 6
  4. customThe solvents were removed under vacuum
  5. additionthe residue treated with saturated NaCl (2 mL)
  6. extractionextracted with 4:1 EtOAc/iPrOH (x4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-5e98ab48ca95480a8d5a4b3eb0fc545d
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

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