Triethylamine → HCID 178436488, compound

HRID 1893360Notes

Reaction equation

HRID 1893360 reaction equation
Cl[C:2](=[N:14][OH:15])[C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([O:11]CC)=[O:10])[CH2:5][CH2:4]1.[CH2:16]=[C:17](N1CCOCC1)[CH2:18][CH3:19].C(N(CC)CC)C>ClCCl>[CH2:18]([C:17]1[O:15][N:14]=[C:2]([C@H:3]2[CH2:4][CH2:5][C@H:6]([C:9]([OH:11])=[O:10])[CH2:7][CH2:8]2)[CH:16]=1)[CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12571421HCID 12571421, compoundHCID 178472360HCID 178472360, compound

Product 1

HCID 178436488HCID 178436488, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of cis/trans-ethyl 4-(chloro(hydroxyimino)methyl)cyclohexanecarboxylate (2.35 g, 10.1 mmol) and 4-(1-methylene-propyl)-morpholine (4.26 g, 30.2 mmol) in dichloromethane (100 ml) was added triethylamine (1.40 ml, 10.1 mmol at 0-5° C. The cooling bath was removed 30 minutes after completed addition. After stirring for 20 h the solvent was evaporated. The residue was redissolved in 6 M aqueous hydrochloric acid solution (100 ml), and the mixture was heated at reflux for 3 h. After cooling to room temperature the reaction mixture was partitioned between crushed ice (300 g) and ethyl acetate (100 ml). The layers were separated. The aqueous layer was extracted with two 100-ml portions of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. Purification with n-heptane/tert-butyl methyl ether as eluent gave the title compound (0.42 g, 19%) as white solid. MS m/e: 222 ([M−H]−)

Workup

  1. customThe cooling bath was removed 30 minutes
  2. additionaddition
  3. customwas evaporated
  4. dissolutionThe residue was redissolved in 6 M aqueous hydrochloric acid solution (100 ml)
  5. temperaturethe mixture was heated
  6. temperatureat reflux for 3 h
  7. customwas partitioned
  8. custombetween crushed ice (300 g) and ethyl acetate (100 ml)
  9. customThe layers were separated
  10. extractionThe aqueous layer was extracted with two 100-ml portions of ethyl acetate
  11. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  12. concentrationconcentrated in vacuo
  13. customPurification with n-heptane/tert-butyl methyl ether as eluent

Sources & evidence

ORD record
ord-d416f06338ff4b59b89acd175e3607f8
Source dataset
uspto-grants-2013_08
Patent number
US08513238B2

Reaction notes

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