Sodium borohydride → HCID 70975527, compound

HRID 2199358Notes

Reaction equation

HRID 2199358 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:25]=[CH:24][CH:23]=[CH:22][C:5]=1[CH:6]=[C:7]1[C:12](=[O:13])[C:11](=[CH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])[CH2:10][NH:9][CH2:8]1>C(O)C>[F:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH:14]=[C:11]1[CH:12]([OH:13])[C:7](=[CH:6][C:5]2[CH:22]=[CH:23][CH:24]=[CH:25][C:4]=2[F:3])[CH2:8][NH:9][CH2:10]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 66993057HCID 66993057, compound

Product 1

HCID 70975527HCID 70975527, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (36 mg, 0.96 mmol) was added to a solution of compound 1 (300 mg, 0.96 mmol) in ethanol at 0° C., in portions. The reaction mixture was stirred at room temperature for 1 h. The solvent was evaporated to dryness. The residue was dissolved in chloroform, and the organic phase was washed with brine and water. The organic layer was dried over sodium sulfate, and concentrated to dryness. The crude product was passed through silica column, and eluted with 70% ethyl acetate in hexanes. The title compound 10 was obtained as colorless thick syrup (296 mg, 98% yield). Rf (60:40 ethyl acetate:hexanes)=0.10. 1H NMR (300 MHz, CDCl3): δ 7.25 (s, 1H), 7.00 (q, 2H, Ar—H, J=7.4), 6.93 (t, 2H, Ar—H, J=7.8), 6.86 (t, 2H, Ar—H, J=7.0), 6.81 (t, 2H, Ar—H, J=7.6), 6.39 (s, 2H, C═CH), 4.66 (s, 1H), 3.61 (d, 2H, J=14.8), 3.25 (d, 2H, J=14.8). 13C NMR (75 MHz, CDCl3): δ 161.42 (d, J=246.2), 144.36, 130.74, 128.50, 128.60, 128.49, 124.31, 124.12, 123.64, 115.43, 115.14, 75.62, 45.68. ESI Mass calculated for C19H17F2NO (M)+313.13. found 313.87.

Workup

  1. customThe solvent was evaporated to dryness
  2. dissolutionThe residue was dissolved in chloroform
  3. washthe organic phase was washed with brine and water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated to dryness
  6. washeluted with 70% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-67e9ec8cd4c647e3a0dc629adf29ed11
Source dataset
uspto-grants-2016_06
Patent number
US09359196B2

Reaction notes

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