Triethylamine → HCID 178501131, compound

HRID 1053822Notes

Reaction equation

HRID 1053822 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]([OH:13])=O)[CH2:7][CH2:6]1)=[O:4].C([N:16](CC)CC)C.ClC(OCC)=O.[OH-].[NH4+]>O1CCCC1.O>[C:11]([C@H:8]1[CH2:9][CH2:10][C@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][CH2:7]1)(=[O:13])[NH2:16]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 14923Ammonium HydroxideHCID 178501163HCID 178501163, compound

Product 1

HCID 178501131HCID 178501131, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (−10° C.) solution of trans-4-(methoxycarbonyl)cyclohexane-1-carboxylic acid (1.01 g, 5.43 mmol) in tetrahydrofuran (25 mL) was sequentially added triethylamine (1.50 mL, 10.9 mmol) and ethyl chloroformate (0.60 mL, 6.2 mmol) under a nitrogen atmosphere and the reaction mixture stirred at room temperature for 3 h. The reaction was then cooled to −10° C., ammonium hydroxide (5.0 mL, 33 mmol) was added and the reaction mixture warmed to room temperature and stirred overnight whereupon the mixture was diluted with water and extracted with ethyl acetate (3×50 mL). The combined organic extracts were dried and concentrated to give the title compound (0.84 g, 84%) as a white solid.

Workup

  1. temperatureThe reaction was then cooled to −10° C.
  2. temperaturethe reaction mixture warmed to room temperature
  3. stirringstirred overnight whereupon the mixture
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. customThe combined organic extracts were dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7d8e0c0e84514216a2b92e84492c2f7e
Source dataset
uspto-grants-2016_07
Patent number
US09394250B2

Reaction notes

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