Hydrochloric Acid → Methyl 1-(4-oxocyclohexyl)propylcarbamate

HRID 1896914Notes

Reaction equation

HRID 1896914 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([CH:11]([NH:14][C:15](=[O:18])[O:16][CH3:17])[CH2:12][CH3:13])[CH2:7][CH2:6]2)[O:4]CC1.Cl>CC#N>[O:4]=[C:5]1[CH2:10][CH2:9][CH:8]([CH:11]([NH:14][C:15](=[O:18])[O:16][CH3:17])[CH2:12][CH3:13])[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68003946HCID 68003946, compound

Product 1

HCID 68003992Methyl 1-(4-oxocyclohexyl)propylcarbamate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of methyl N-(1-1,4-dioxaspiro[4.5]decan-8-ylpropyl)carbamate (as prepared in the previous step, 39 mg, 0.15 mmol, 1.00 equiv) in CH3CN (5 mL) and HCl (2M, 1 mL) was stirred for 2 h at room temperature. The resulting mixture was concentrated under vacuum. The residue was diluted with 10 mL of aq. sodium bicarbonate (1M). The resulting solution was extracted with 2×20 mL of dichloromethane. The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under vacuum to give the title compound as a yellow oil.

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum
  2. additionThe residue was diluted with 10 mL of aq. sodium bicarbonate (1M)
  3. extractionThe resulting solution was extracted with 2×20 mL of dichloromethane
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-04d4945abb924f74bf55f70d52fffaa4
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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