Ethyl Acetate → 1-(5-Bromo-3,4-dihydroquinolin-1(2H)-yl)-4-hydroxybutan-1-one

HRID 2175281Notes

Reaction equation

HRID 2175281 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][N:7]2[C:12](=[O:19])[CH2:13][CH2:14][C:15](OC)=[O:16].[BH4-].[Na+].C(OCC)(=O)C>CO>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][N:7]2[C:12](=[O:19])[CH2:13][CH2:14][CH2:15][OH:16]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 4311764Sodium borohydride2×HCID 86712596Methyl 4-(5-bromo-3,4-dihydroquinolin-1(2H)-yl)-4-oxobutanoate

Product 1

HCID 709827651-(5-Bromo-3,4-dihydroquinolin-1(2H)-yl)-4-hydroxybutan-1-oneYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of methyl 4-(5-bromo-3,4-dihydroquinolin-1(2H)-yl)-4-oxobutanoate (0.9 g, 2.76 mmol) in MeOH (30 mL) was added sodium borohydride (2.088 g, 55.2 mmol), and the resulting mixture was stirred at room temperature for 30 min. After this time, additional sodium borohydride (1.566 g, 41.4 mmol) was added slowly and the reaction was stirred for another 30 min. The reaction mixture was quenched with HCl and extracted with ethyl acetate. The combined organic layer was dried over anhydrous MgSO4, filtered, and concentrated. The resulting residue was purified by flash chromatography (0-100% ethyl acetate:hexanes then 10% CH3OH:ethyl acetate) to afford the title compound (0.6 g, 73% yield) as a colorless oil. LCMS, [M+H]+=298.0. 1H NMR (400 MHz, MeOD) δ 7.49 (d, J=8.1 Hz, 1H), 7.44 (br. s, 1H), 7.17 (t, J=8.1 Hz, 1H), 3.86-3.80 (m, 2H), 3.61 (t, J=6.2 Hz, 2H), 2.89 (t, J=6.9 Hz, 2H), 2.68 (t, J=7.4 Hz, 2H), 2.10-2.01 (m, 2H), 1.95-1.85 (m, 2H).

Workup

  1. stirringthe reaction was stirred for another 30 min
  2. customThe reaction mixture was quenched with HCl
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layer was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by flash chromatography (0-100% ethyl acetate

Sources & evidence

ORD record
ord-c087dc0d793f44b293973a537502112d
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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