Cyclopentylamine → Tert-butyl 2-(cyclopentylamino)acetate

HRID 543259Notes

Reaction equation

HRID 543259 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]>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

5

Reactant 3

HCID 2906CyclopentylamineHCID 8471TriethylamineHCID 79177tert-Butyl bromoacetate

Product 1

HCID 13298943Tert-butyl 2-(cyclopentylamino)acetateYield 65%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution containing 75 g (0.88 mol) of cyclopentylamine and 100 g (1.0 mol) of triethylamine in 500 ml of ether at 0° C. was slowly added 136 g (0.70 mol) of t-butyl bromoacetate in 200 ml of ether. After stirring at room temperature for 6 hours, the mixture was filtered, washed with water, and concentrated in vacuo. The residue was acidified with 5% aqueous HCl, washed with ether, rendered basic with 5% aqueous K2CO3, and extracted with ether. The ethereal solution was then washed with water, dried over MgSO4, and concentrated in vacuo to give 90 g (65%) of N-cyclopentylglycine, t-butyl ester as an oil which crystallized on standing.

Workup

  1. filtrationthe mixture was filtered
  2. washwashed with water
  3. concentrationconcentrated in vacuo
  4. washwashed with ether
  5. extractionextracted with ether
  6. washThe ethereal solution was then washed with water
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2642eb0aa3654565bca5b1c933728eb5
Source dataset
uspto-grants-1987_04
Patent number
US04661515

Reaction notes

Loading…