Cyclopentylamine → Methyl 2-(cyclopentylamino)acetate

HRID 79139Notes

Reaction equation

HRID 79139 reaction equation
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].[CH:7]1([NH2:12])[CH2:11][CH2:10][CH2:9][CH2:8]1.C(N(CC)CC)C>C1COCC1>[CH:7]1([NH:12][CH2:2][C:3]([O:5][CH3:6])=[O:4])[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 2906CyclopentylamineHCID 8471TriethylamineHCID 60984Methyl bromoacetate

Product 1

HCID 22080509Methyl 2-(cyclopentylamino)acetateYield 68.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of methyl bromoacetate (17.4 mL, 188 mmol) in THF (40 mL) was dropwise added to a solution of cyclopentylamine (18.6 mL, 188 mmol) and triethylamine (26.1 mL, 188 mmol) in THF (150 mL) at 0° C. Following addition, the reaction was allowed to reach room temperature and was stirred overnight. The triethylammonium salts were filtered and rinsed with scant THF. The combined filtrates were concentrated in vacuo. The desired product was distilled from the residuals under reduced pressure to yield 20.2 g of compound 225 (68% yield). 1H NMR (500 MHz, CDCl3) δ ppm 3.73 (s, 3 H) 3.41 (s, 2 H) 3.00-3.13 (m, J=12.90, 6.39, 6.39 Hz, 1 H) 1.77-1.87 (m, 2 H), 1.67-1.74 (m, 2 H) 1.48-1.59 (m, 2 H) 1.29-1.41 (m, 2 H) ppm.

Workup

  1. additionaddition
  2. customto reach room temperature
  3. filtrationThe triethylammonium salts were filtered
  4. washrinsed with scant THF
  5. concentrationThe combined filtrates were concentrated in vacuo
  6. distillationThe desired product was distilled from the residuals under reduced pressure

Sources & evidence

ORD record
ord-9259a604d1fe41a2ba980c5de40795f8
Source dataset
uspto-grants-2014_09
Patent number
US08841312B2

Reaction notes

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