Lithium borohydride → 4-{2-[(5-Methyl-furan-2-ylmethyl)-amino]-quinolin-5-yl}-butan-1-ol

HRID 1669722Notes

Reaction equation

HRID 1669722 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][CH2:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH:9]=[CH:10][C:11]([NH:17][CH2:18][C:19]1[O:20][C:21]([CH3:24])=[CH:22][CH:23]=1)=[N:12]2.[BH4-].[Li+]>O1CCCC1>[CH3:24][C:21]1[O:20][C:19]([CH2:18][NH:17][C:11]2[CH:10]=[CH:9][C:8]3[C:13](=[CH:14][CH:15]=[CH:16][C:7]=3[CH2:6][CH2:5][CH2:4][CH2:3][OH:2])[N:12]=2)=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 442181534-{2-[(5-Methyl-furan-2-ylmethyl)-amino]-quinolin-5-yl}-butyric acid methyl ester

Product 1

HCID 442181544-{2-[(5-Methyl-furan-2-ylmethyl)-amino]-quinolin-5-yl}-butan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-{2-[(5-Methyl-furan-2-ylmethyl)-amino]-quinolin-5-yl}-butyric acid methyl ester (100 mg, 0.3 mmol) was dissolved in 10 mL dry tetrahydrofurane. Lithiumborohydride (100 mg, 4.5 mmol) was added and the reaction mixture was refluxed overnight. The reaction mixture was quenched by addition of IN hydrochloride solution and refluxed for 30 minutes. The mixture was then adjusted to pH 10 by addition of 25% solution of ammonium hydroxide and extracted three times with ethyl acetate (100 mL each). The organic phases were pooled, dried with sodium sulfate, filtered and evaporated. The residue was purified by flash chromatography on silica gel (heptane/ethyl acetate 100:0→0:100 gradient). The title compound was obtained as a light yellow oil (67 mg, 73%), MS: m/e=311.0 (M+H+).

Workup

  1. temperaturethe reaction mixture was refluxed overnight
  2. customThe reaction mixture was quenched by addition of IN hydrochloride solution
  3. temperaturerefluxed for 30 minutes
  4. additionThe mixture was then adjusted to pH 10 by addition of 25% solution of ammonium hydroxide
  5. extractionextracted three times with ethyl acetate (100 mL each)
  6. dry with materialdried with sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by flash chromatography on silica gel (heptane/ethyl acetate 100:0→0:100 gradient)

Sources & evidence

ORD record
ord-1a947c20bfb44659b8028922e3f6e72d
Source dataset
uspto-grants-2011_08
Patent number
US07989628B2

Reaction notes

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