Diisobutylaluminumhydride → (E)-2-Fluoro-3-(6-isopropyl-4,4-dimethyl-1-n-propyl-1,2,3,4-tetrahydro-quinolin-8-yl)-but-2-enoic acid ethyl ester

HRID 1582090Notes

Reaction equation

HRID 1582090 reaction equation
[CH2:1]([O:3][C:4](=[O:26])/[C:5](/[F:25])=[C:6](\[C:8]1[CH:9]=[C:10]([CH:22]([CH3:24])[CH3:23])[CH:11]=[C:12]2[C:17]=1[N:16]([CH2:18][CH3:19])[CH2:15][CH2:14][C:13]2([CH3:21])[CH3:20])/[CH3:7])[CH3:2].[H-].[CH2:28]([Al+]CC(C)C)C(C)C>C1COCC1>[CH2:1]([O:3][C:4](=[O:26])/[C:5](/[F:25])=[C:6](\[C:8]1[CH:9]=[C:10]([CH:22]([CH3:24])[CH3:23])[CH:11]=[C:12]2[C:17]=1[N:16]([CH2:18][CH2:19][CH3:28])[CH2:15][CH2:14][C:13]2([CH3:21])[CH3:20])/[CH3:7])[CH3:2]

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 69897280(E)-3-(1-Ethyl-6-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-8-yl)-2-fluro-but-2-enoic acid ethyl ester2×

Product 1

HCID 69898585(E)-2-Fluoro-3-(6-isopropyl-4,4-dimethyl-1-n-propyl-1,2,3,4-tetrahydro-quinolin-8-yl)-but-2-enoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (E)-3-(1-ethyl-6-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-8-yl)-2-fluoro-but-2-enoic acid ethyl ester (Intermediate 15, 199 mg, 0.55 mmol) in 10 ml of anhydrous THF under argon at 0° C. was added a 1.0 M solution of diisobutylaluminum hydride (2.20 ml, 2.20 mmol) in hexanes. The resulting mixture was stirred at 0° C. to 25° C. for 1 h. The reaction was cooled to 0 ° C. and quenched slowly with saturated NH4Cl (0.5 ml), Celite (200 mg), and diluted with diethyl ether (10 ml). The resulting mixture was stirred at 25 ° C. for 1 hour. The product was filtered through a pad of Celite. The solution was dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography using ethyl acetate: hexane (1:4) to yield the title compound as a yellow oil.

Workup

  1. customquenched slowly with saturated NH4Cl (0.5 ml), Celite (200 mg)
  2. additiondiluted with diethyl ether (10 ml)
  3. stirringThe resulting mixture was stirred at 25 ° C. for 1 hour
  4. filtrationThe product was filtered through a pad of Celite
  5. dry with materialThe solution was dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-c46843cd5e2a40c585b6aa4b357c28aa
Source dataset
uspto-grants-2004_05
Patent number
US06734193B1

Reaction notes

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