Triethylamine → HCID 62499585, compound

HRID 625441Notes

Reaction equation

HRID 625441 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][OH:7].Br[CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].C(N(CC)CC)C>C1COCC1>[OH:7][CH2:6][CH2:5][O:4][CH2:3][CH2:2][NH:1][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13578DiglycolamineHCID 79177tert-Butyl bromoacetate

Product 1

HCID 62499585HCID 62499585, compoundYield 23.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-(2-aminoethoxy)ethanol (11 g, 104.62 mmol, 1.00 equiv) was dissolved in THF (300 mL) and cooled to 0° C. To the stirring solution was added dropwise tert-butyl 2-bromoacetate (20 g, 102.54 mmol, 1.00 equiv) and then triethylamine (15.5 g, 153.18 mmol, 1.50 equiv) dropwise The solution was then stirred for 16 h at room temperature. The solvent was removed and the residue then dissolved in DCM and washed twice with brine, then dried over anhydrous sodium sulfate and solvent removed. The residue was applied onto a silica gel column with dichloromethane/methanol (20:1) as eluent. This resulted in 5.25 g (16%) of the product as a yellow oil. MS (ES, m/z) 220 [M+H]+

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue then dissolved in DCM
  3. washwashed twice with brine
  4. dry with materialdried over anhydrous sodium sulfate and solvent
  5. customremoved

Sources & evidence

ORD record
ord-9b8dafd6d5cf46b5bfc327db87de5cb2
Source dataset
uspto-grants-2016_04
Patent number
US09301951B2

Reaction notes

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