Ethanolamine → HCID 57487387, compound

HRID 348994Notes

Reaction equation

HRID 348994 reaction equation
[CH2:1]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([O:17][CH3:18])=[O:16])[CH:13]=2)[N:8]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:7][C:6]1=O)[CH2:2][CH2:3][CH3:4].C12CCCC(CCC1)B12[H]B2(C3CCCC2CCC3)[H]1.C(CN)O>O1CCCC1>[CH2:1]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([O:17][CH3:18])=[O:16])[CH:13]=2)[N:8]([C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 57487386HCID 57487386, compound

Product 1

HCID 57487387HCID 57487387, compoundYield 37.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-tert-butyl 6-methyl 4-butyl-3-oxo-3,4-dihydroquinoxaline-1,6(2H)-dicarboxylate (440 mg) and 9-BBN dimer (600 mg) in tetrahydrofuran (10 mL) was heated at 65° C. for 10 h. The mixture was cooled to room temperature, ethanolamine (0.15 mL) was added and the resulting solution was concentrated under reduced pressure. The residue was washed with hexanes, filtered, and the filtrate was concentrated under reduced pressure. Purification by flash column chromatography (silica, 1:9 ethyl acetate/hexanes) afforded 158 mg of the title compound: 1H NMR (300 MHz, CDCl3) δ 7.50, 7.34, 7.28, 3.88, 3.77, 3.38–3.30, 1.65–1.51, 1.42–1.34, 0.99–0.94.

Workup

  1. concentrationthe resulting solution was concentrated under reduced pressure
  2. washThe residue was washed with hexanes
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customPurification by flash column chromatography (silica, 1:9 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-13799ebfe1e5413da95fb287b027cf6d
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Reaction notes

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