Tert-Butylamine → Tert-butylamino-pyridin-3-yl-acetic acid ethyl ester

HRID 352215

Reaction equation

HRID 352215 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH:5](Br)[C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)[CH3:2].[C:14]([NH2:18])([CH3:17])([CH3:16])[CH3:15].CCN(CC)CC>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:13])[CH:5]([NH:18][C:14]([CH3:17])([CH3:16])[CH3:15])[C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 21985933Ethyl 2-bromo-2-(pyridin-3-yl)acetate

Product 1

HCID 69850097Tert-butylamino-pyridin-3-yl-acetic acid ethyl esterYield 41.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bromo-pyridin-3-yl-acetic acid ethyl ester (2.4 g; 9.8 mmol) was reacted in refluxing CH2Cl2, overnight with tert-butylamine (6.2 mL; 55.8 mmol; 6 equiv) and Et3N (2.8 mL; 19.6 mmol; 2 equiv). The reaction solution was evaporated to dryness, dissolved in CH2Cl2, washed six times with saturated NaHCO3 (aq), washed once with saturated NaCl (aq), dried with Na2SO4, filtered, and concentrated in vacuo. The resulting brown oil was purified with silica gel chromatography in a 6×8 cm glass column using a 30% EtOAc/hexanes (v/v) mobile phase. A total of 955 mg desired product was isolated (41% yield). MS(ES) calc'd: [M+H]+=237.1 m/z. Found: 237.1 m/z.

Workup

  1. customThe reaction solution was evaporated to dryness
  2. dissolutiondissolved in CH2Cl2
  3. washwashed six times with saturated NaHCO3 (aq)
  4. washwashed once with saturated NaCl (aq)
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting brown oil was purified with silica gel chromatography in a 6×8 cm glass column

Sources & evidence

ORD record
ord-3499288dff3147a4924a45c2b553ec54
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Linked notes

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