Potassium Carbonate → HCID 10466952, compound

HRID 2176946Notes

Reaction equation

HRID 2176946 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-2f49edafafcb4a81a9ed337b78033ea4
Source dataset
uspto-grants-2015_06
Patent number
US09067888B2

Reaction notes

Loading…