Acetic Anhydride → rac-(1R,3S)-3-(acetamidomethyl)cyclopentane-1-carboxylic acid

HRID 2187995Notes

Reaction equation

HRID 2187995 reaction equation
[NH2:1][CH2:2][C@@H:3]1[CH2:7][CH2:6][C@H:5]([C:8]([OH:10])=[O:9])[CH2:4]1.[C:11](OC(=O)C)(=[O:13])[CH3:12]>N1C=CC=CC=1>[CH3:12][C:11]([NH:1][CH2:2][C@@H:3]1[CH2:7][CH2:6][C@H:5]([C:8]([OH:10])=[O:9])[CH2:4]1)=[O:13]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 42614337rac-(1R,3S)-3-(aminomethyl)cyclopentane-1-carboxylic acid

Product 1

HCID 12041173rac-(1R,3S)-3-(acetamidomethyl)cyclopentane-1-carboxylic acidYield 97%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of cis-3-aminomethylcyclopentancarboxylic acid (0.2 g, 1.4 mmol) in pyridine (about 5 mL) was added acetic anhydride (about 1 mL) and the mixture stirred at about 70° C. for about 2 h. The solvent was removed under reduced pressure, water was added several times and evaporated in vacuo. A light, viscous oil was obtained and dried in vacuo over acetone reflux to give 0.25 g (97%) of cis-3-[(methylcarbonylamino)methyl]cyclopentancarboxylic acid.

Workup

  1. customThe solvent was removed under reduced pressure, water
  2. additionwas added several times
  3. customevaporated in vacuo
  4. customA light, viscous oil was obtained
  5. dry with materialdried in vacuo over acetone
  6. temperaturereflux

Sources & evidence

ORD record
ord-8b99720d62824a7bab8a81d775bd63cc
Source dataset
uspto-grants-2002_06
Patent number
US06410594B1

Reaction notes

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