Ethyl 4-oxocyclohexanecarboxylate → HCID 17963321, compound

HRID 969547Notes

Reaction equation

HRID 969547 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[Cl:15])[O:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.O=[C:17]1[CH2:22][CH2:21][CH:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:19][CH2:18]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C1COCC1.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[Cl:15])[O:5][CH:6]1[CH2:11][CH2:10][N:9]([CH:17]2[CH2:22][CH2:21][CH:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:19][CH2:18]2)[CH2:8][CH2:7]1

Participants

7

Reactant 4

HCID 317638Ethyl 4-oxocyclohexanecarboxylateHCID 516892Sodium BicarbonateHCID 37320424-(3,4-Dichlorophenoxy)piperidineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 17963321HCID 17963321, compoundYield 67.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-(3,4-Dichlorophenoxy)piperidine (Method B, 1.44 g), ethyl 4-oxocyclohexanecarboxylate (1.0 g) and acetic acid (0.34 ml) were combined in THF 10 ml and the solution was cooled in ice. Sodium triacetoxy borohydride (1.45 g) was added and the mixture was stirred overnight and allowed to come to ambient temperature. The reaction mixture was poured onto a stirred saturated aq solution of sodium bicarbonate. The mixture was extracted with ethyl acetate thrice, the organic phases were washed with brine, dried, filtered and evaporated. The residue was purified on an SCX cartridge (International Sorbent Technology Isolute® Flash SCX-2), washed with methanol and then product eluted with 0.7M ammonia in methanol. Further purification by chromatography (silica, 90:9:1 DCM:methanol:triethylamine) gave the subtitle compound (1.59 g; MS [M+H]+ (APCI+) 400/402) as a mixture of cis/trans isomers.

Workup

  1. temperaturethe solution was cooled in ice
  2. customto come to ambient temperature
  3. extractionThe mixture was extracted with ethyl acetate thrice
  4. washthe organic phases were washed with brine
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified on an SCX cartridge (International Sorbent Technology Isolute® Flash SCX-2)
  9. washwashed with methanol
  10. washproduct eluted with 0.7M ammonia in methanol
  11. customFurther purification by chromatography (silica, 90:9:1 DCM:methanol:triethylamine)

Sources & evidence

ORD record
ord-9df3cfb2dfec4536b00ed73d377aa138
Source dataset
uspto-grants-2007_12
Patent number
US07307090B2

Reaction notes

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