Hydrochloric Acid → Tert-butyl 2-(cyclopentylamino)acetate

HRID 620223Notes

Reaction equation

HRID 620223 reaction equation
[CH:1]1([NH2:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Br[CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].Cl>CCOCC>[CH:1]1([NH:6][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2906CyclopentylamineHCID 8471TriethylamineHCID 79177tert-Butyl bromoacetate

Product 1

HCID 13298943Tert-butyl 2-(cyclopentylamino)acetate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Cyclopentyl amine (50.0 g, 587 mmols) was dissolved in anhydrous ether (500 ml) and triethylamine (69.3 g, 685 mols) was added. The resulting solution was cooled in an ice bath and then tert-butyl bromoacetate (95.4 g, 489 mmols) in ether (150 ml) was added slowly over approximately three hours. The reaction mixture was allowed to stir overnight at room temperature. The reaction was acidified to pH 1 with aqueous hydrochloric acid and the layers were separated. The aqueous layer was washed with ethyl acetate and then basified to pH 10 with aqueous ammonium hydroxide. The product was extracted several times into methylene chloride and the combined organic extract was washed twice with water, once with brine, dried over magnesium sulfate, filtered, and evaporated to yield the desired product as a slightly yellow oil (56.9 g, 58.4%).

Workup

  1. temperatureThe resulting solution was cooled in an ice bath
  2. customthe layers were separated
  3. washThe aqueous layer was washed with ethyl acetate
  4. extractionThe product was extracted several times into methylene chloride
  5. extractionthe combined organic extract
  6. washwas washed twice with water, once with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-d7b5c37ef22c4ab8bffafc9306098796
Source dataset
uspto-grants-1989_04
Patent number
US04820729

Reaction notes

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