Ethanolamine → HCID 59403473, compound

HRID 1514252Notes

Reaction equation

HRID 1514252 reaction equation
[Br:1][C:2]1[C:3]([OH:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[NH2:11][CH2:12][CH2:13][OH:14].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:4]([CH2:5][NH:11][CH2:12][CH2:13][OH:14])[C:3]=1[OH:10]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 5049666Sodium triacetoxyborohydrideHCID 109105553-Bromo-2-hydroxybenzaldehyde

Product 1

HCID 59403473HCID 59403473, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-bromo-2-hydroxybenzaldehyde (Preparation 98) (9.6 g, 47.8 mmol) in tetrahydrofuran (250 ml) at 0° C. under nitrogen was added 2-aminoethanol (3.02 ml, 50.1 mmol) then finely powdered sodium triacetoxyborohydride (10.6 g, 50.1 mmol) and the resulting mixture was stirred at 0° C. for 1 h, then stirred overnight and concentrated in vacuo. The residue was triturated under dichloromethane (˜200 mL) and insoluble material was filtered off. The organic phase was concentrated in vacuo and the residue purified using an SCX column to give the title compound as a white solid (10.1 g). MS (ES) C9H1079BrNO2 requires 243 found 244 [M+H]+.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was triturated under dichloromethane (˜200 mL)
  3. filtrationinsoluble material was filtered off
  4. concentrationThe organic phase was concentrated in vacuo
  5. customthe residue purified

Sources & evidence

ORD record
ord-ced11fc66f2b4c08882d3b439a1a4128
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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