Potassium Carbonate → HCID 10466952, compound

HRID 1896310Notes

Reaction equation

HRID 1896310 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][C@@H:4]([C:7]([O:9][CH3:10])=[O:8])[CH2:3]1.[C:11](=[O:14])([O-])[O-:12].[K+].[K+]>C1COCC1.O>[CH3:10][O:9][C:7]([C@@H:4]1[CH2:5][CH2:6][C@H:2]([NH:1][C:11](=[O:14])[O:12][C:4]([CH3:7])([CH3:5])[CH3:3])[CH2:3]1)=[O:8]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 10464431(1R,3S)-methyl 3-aminocyclopentanecarboxylate

Product 1

HCID 10466952HCID 10466952, compoundYield 172.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Boc-anhydride (2.90 ml, 13.1 mmol) was added to a solution of (1R,3S)-methyl 3-aminocyclopentanecarboxylate (1.70 g, 11.9 mmol) and potassium carbonate (3.29 g, 23.8 mmol) in THF (10 ml), water (20 ml) and stirred for 24 h. The reaction mixture was extracted with DCM (2×50 ml). The combined organic layer was washed with water (20 ml), brine solution (20 ml), dried over anhydrous sodium sulfate, filtered and concentrated under vacuo to afford 2.5 g (87%) of tert-butyl (1S,3R)-3-(methoxycarbonyl)cyclopentylcarbamate as a colorless liquid.

Workup

  1. extractionThe reaction mixture was extracted with DCM (2×50 ml)
  2. washThe combined organic layer was washed with water (20 ml), brine solution (20 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuo

Sources & evidence

ORD record
ord-33b6f51af6ad477e88082a844f08a7a9
Source dataset
uspto-grants-2013_08
Patent number
US08518948B2

Reaction notes

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