Triethylamine → HCID 55281435, compound

HRID 656243Notes

Reaction equation

HRID 656243 reaction equation
[C@H:1]1(C(O)=O)[C:3]2([CH2:8][CH2:7][O:6][CH2:5][CH2:4]2)[CH2:2]1.C([N:14](CC)CC)C.ClC(OCC)=O.[N-]=[N+]=[N-].[Na+]>O1CCCC1.O>[C@H:1]1([NH2:14])[C:3]2([CH2:8][CH2:7][O:6][CH2:5][CH2:4]2)[CH2:2]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 57429835HCID 57429835, compound

Product 1

HCID 55281435HCID 55281435, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 0.528 g of (R)-6-oxaspiro[2.5]-octane-1-carboxylic acid in 5 ml of tetrahydrofuran is mixed with 1.20 ml of triethylamine, and the solution is then cooled to 0° C. The solution is mixed with 0.657 ml of ethyl chloroformate, and the reaction mixture is stirred at 0° C. for 1 hour. A solution of 4.44 g of sodium azide in 5 ml of water is added and the reaction mixture is stirred at 0° C. for a further hour. The reaction mixture is diluted with water and extracted with tert-butyl methyl ether. The combined extracts are washed with brine, dried with sodium sulphate and evaporated. The residue is taken up in 5 ml of benzene, and the solution is heated to reflux for 2 hours and then evaporated. The residue is dissolved in 5 ml of tetrahydrofuran, and 5 ml of water and 0.347 g of lithium hydroxide are added. The reaction mixture is stirred at room temperature for 3 hours and then adjusted to pH 2 with 4M HCl. The tetrahydrofuran is distilled off, and the aqueous residue is adjusted to pH 12 with 2M NaOH. The aqueous phase is extracted with dichloromethane, and the combined organic extracts are dried over sodium sulphate and evaporated. The title compound is obtained as a yellow oil which is employed without further purification in the next stage. Rf=0.26 (dichloro-methane-methanol-conc. ammonia 25% 200:20:1).

Workup

  1. stirringthe reaction mixture is stirred at 0° C. for a further hour
  2. extractionextracted with tert-butyl methyl ether
  3. washThe combined extracts are washed with brine
  4. dry with materialdried with sodium sulphate
  5. customevaporated
  6. temperaturethe solution is heated
  7. temperatureto reflux for 2 hours
  8. customevaporated
  9. dissolutionThe residue is dissolved in 5 ml of tetrahydrofuran
  10. addition5 ml of water and 0.347 g of lithium hydroxide are added
  11. stirringThe reaction mixture is stirred at room temperature for 3 hours
  12. distillationThe tetrahydrofuran is distilled off
  13. extractionThe aqueous phase is extracted with dichloromethane
  14. dry with materialthe combined organic extracts are dried over sodium sulphate
  15. customevaporated

Sources & evidence

ORD record
ord-eaa20b9dd59e41e28c135aede223d3f9
Source dataset
uspto-grants-2011_12
Patent number
US08071651B2

Reaction notes

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