Hydrochloric Acid → Benzyl (4-oxocyclohexyl)(propyl)carbamate

HRID 1896865Notes

Reaction equation

HRID 1896865 reaction equation
[CH2:1]([N:4]([CH:15]1[CH2:24][CH2:23][C:18]2(OCC[O:19]2)[CH2:17][CH2:16]1)[C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:2][CH3:3].Cl>C(#N)C>[O:19]=[C:18]1[CH2:23][CH2:24][CH:15]([N:4]([CH2:1][CH2:2][CH3:3])[C:5](=[O:14])[O:6][CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58562547Benzyl propyl(1,4-dioxaspiro[4.5]decan-8-yl)carbamate

Product 1

HCID 58562893Benzyl (4-oxocyclohexyl)(propyl)carbamate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Benzyl propyl(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 (×4). 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 (×4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-502fa092e3154e4092633d1221a04065
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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