Methanol → HCID 12147026, compound

HRID 1836328Notes

Reaction equation

HRID 1836328 reaction equation
[F:1][C:2]([F:26])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:3][NH:4][C:5]1[C:6](=[O:19])[N:7]([CH2:12][CH2:13][C:14](OCC)=[O:15])[C:8]([CH3:11])=[CH:9][N:10]=1.CO.[BH4-].[Na+]>O1CCCC1.O.ClCCl>[F:26][C:2]([F:1])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:3][NH:4][C:5]1[C:6](=[O:19])[N:7]([CH2:12][CH2:13][CH2:14][OH:15])[C:8]([CH3:11])=[CH:9][N:10]=1

Participants

7

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 12147025HCID 12147025, compound

Product 1

HCID 12147026HCID 12147026, compoundYield 93.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(2,2-difluoro-2-phenylethylamino)-1-[(2-ethoxycarbonyl)ethyl]-6-methylpyrazinone (2-11) (0.37 g, 1.01 mmol) in tetrahydrofuran (10 mL) containing 5% methanol, was added sodium borohydride (0.229 g, 6.07 mmol) at room temperature. The reaction mixture was stirred for 5 hours. Then 2 mL of water was added and the mixture was fractionated between dichloromethane and water. The organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude residue was purified using a silica gel column chromatography with ethyl acetate/n-hexane (1:1) as eluent to afford the title compound (0.305 g, 93%) as a pale yellow solid. Rf 0.28 (MeOH/CH2Cl2 5/95); 1H-NMR (CDCl3): δ 1.85 (quintet, J=6.4 Hz, 2H), 2.19 (d, J=1.2 Hz, 3H), 3.47 (q, J=6.4 Hz, 2H), 3.65 (t, J=6.8 Hz, 1H), 4.05 (dt, J=6.4, 14.0 Hz, 2H), 4.12 (t, J=6.4 Hz, 2H), 6.14 (t, J=6.4 Hz, 1H), 6.68(d, J=0.8 Hz, 1H), 7.23-7.41 (m, 3H), 7.49-7.52 (m, 2H).

Workup

  1. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  2. concentrationconcentrated under reduced pressure
  3. customThe crude residue was purified

Sources & evidence

ORD record
ord-9c7c552b0f1549b3a8b0665d1793b878
Source dataset
uspto-grants-2004_08
Patent number
US06777431B2

Reaction notes

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