Sulfuric Acid → 1-Cyclopentyl 1-aminocyclopentanecarboxylate

HRID 1622965Notes

Reaction equation

HRID 1622965 reaction equation
[NH2:1][C:2]1([C:7]([OH:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3]1.S(=O)(=O)(O)O>C1(O)CCCC1>[NH2:1][C:2]1([C:7]([O:9][CH:2]2[CH2:6][CH2:5][CH2:4][CH2:3]2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 2901Cycloleucine

Product 1

HCID 581390221-Cyclopentyl 1-aminocyclopentanecarboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 7298CyclopentanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 1-aminocyclopentanecarboxylic acid (2.58 g, 19.97 mmol) in cyclopentanol (20 ml), was added concentrated sulfuric acid (2.15 g, 21.97 mmol) and the mixture stirred overnight at 70° C. The reaction was allowed to cool to RT and the cyclopentanol removed under reduced pressure. The residue was dissolved in EtOAc (30 ml) and washed with sat. NaHCO3 (30 ml) and water (3×20 ml) then dried (MgSO4), filtered and concentrated in vacuo to leave a dark yellow oil. Purification by column chromatography (15% 1.2 M NH3/MeOH in EtOAc) afforded the desired product (1.97 g, 50% yield).

Workup

  1. temperatureto cool to RT
  2. customthe cyclopentanol removed under reduced pressure
  3. dissolutionThe residue was dissolved in EtOAc (30 ml)
  4. washwashed with sat. NaHCO3 (30 ml) and water (3×20 ml)
  5. dry with materialthen dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto leave a dark yellow oil
  9. customPurification by column chromatography (15% 1.2 M NH3/MeOH in EtOAc)

Sources & evidence

ORD record
ord-ce05710631c14601999742a04f4a9096
Source dataset
uspto-grants-2014_07
Patent number
US08778953B2

Reaction notes

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