Ethylmorpholine → HCID 20487949, compound

HRID 1995744Notes

Reaction equation

HRID 1995744 reaction equation
Cl.[C:2]([CH:6]1[CH:11]2[CH2:12][CH:8]([CH2:9][CH2:10]2)[NH:7]1)([O:4][CH3:5])=[O:3].[C:13]([CH2:17][CH2:18][CH:19]([CH3:23])[C:20](O)=[O:21])([O:15][CH3:16])=[O:14].C(N1CCOCC1)C.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C.O1CCCC1>[C:2]([CH:6]1[CH:11]2[CH2:12][CH:8]([CH2:9][CH2:10]2)[N:7]1[C:20](=[O:21])[CH:19]([CH3:23])[CH2:18][CH2:17][C:13]([O:15][CH3:16])=[O:14])([O:4][CH3:5])=[O:3]

Participants

8

Reactant 5

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 131928974-Carbomethoxy-2-methylbutanoic acidHCID 20487957Methyl 2-azabicyclo[2.2.1]heptane-3-carboxylate hydrochloride

Product 1

HCID 20487949HCID 20487949, compoundYield 57.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3.83 g (0.02 m) of 3-carbomethoxy-2-azabicyclo[2.2.1]heptane hydrochloride from Example 1, 3.29 g (0.02 m) of 4-carbomethoxy-2-methylbutanoic acid, 2.3 g of N-ethylmorpholine, 5.4 g of 1-hydroxybenzotriazole, 4.13 g of dicyclohexylcarbodiimide and 60 ml of dry tetrahydrofuran was prepared with cooling and stirring, then, allowed to stir at room temperature for 18 hours. The mixture was filtered. The filtrate was evaporated to give a syrup which was dissolved in ethyl acetate and washed with 10% acetic acid/water and water. A solid separated. The ethyl acetate extract was further washed with 5% sodium bicarbonate solution and brine, then, dried and evaporated under reduced pressure to give 3.41 g (57%) of 3-carbomethoxy-2-(4-carbomethoxy-2-methylbutanoyl)-2-azabicyclo[2.2.1]heptane, mE 297.

Workup

  1. customwas prepared
  2. temperaturewith cooling
  3. stirringto stir at room temperature for 18 hours
  4. filtrationThe mixture was filtered
  5. customThe filtrate was evaporated
  6. customto give a syrup which
  7. washwashed with 10% acetic acid/water and water
  8. customA solid separated
  9. extractionThe ethyl acetate extract
  10. washwas further washed with 5% sodium bicarbonate solution and brine
  11. customdried
  12. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-83a1bb81f19b4c309f8086510a1c8229
Source dataset
uspto-grants-1983_09
Patent number
US04405787

Reaction notes

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