Sodium borohydride → HCID 11610805, compound

HRID 1173390Notes

Reaction equation

HRID 1173390 reaction equation
[CH:1]1([CH2:4][N:5]([CH2:18][CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([CH:27]=[O:28])=[CH:23][CH:22]=2)[C:6]2[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[C:8]([C:14]([F:17])([F:16])[F:15])[CH:7]=2)[CH2:3][CH2:2]1.[BH4-].[Na+]>CO>[CH:1]1([CH2:4][N:5]([CH2:18][CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([CH2:27][OH:28])=[CH:23][CH:22]=2)[C:6]2[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[C:8]([C:14]([F:16])([F:17])[F:15])[CH:7]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86623730HCID 86623730, compound

Product 1

HCID 11610805HCID 11610805, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-((cyclopropylmethyl){2-[(4-formylphenyl)oxy]ethyl}amino)-2-(trifluoromethyl)benzonitrile (0.0701 g, 0.181 mmol) in MeOH (1 mL) at 0° C. was added NaBH4 (0.0034 g, 0.090 mmol) in one portion. The mixture was stirred 15 min, quenched by dropwise addition of NH4Cl (sat'd) and poured into water. The whole was extracted with CH2Cl2 (×3), combined organic portions were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording 0.0556 g of the title compound as a colorless film: 1H NMR (300 MHz, CDCl3) δ 7.58 (d, J=8.9 Hz, 1H), 7.28 (app. d, J=8.4 Hz, 2H), 7.12 (d, J=2.4 Hz, 1H), 6.91 (dd, J=8.9, 2.5 Hz, 1H), 6.83 (app. d, J=8.5 Hz, 2H), 4.61 (s, 2H), 4.16 (t, J=5.6 Hz, 2H), 3.91 (t, J=5.6 Hz, 2H), 3.40 (d, J=6.3 Hz, 2H), 1.69 (bs, 1H), 1.14-0.99 (m, 1H), 0.69-0.59 (m, 2H), 0.36-0.28 (m, 2H).

Workup

  1. customquenched by dropwise addition of NH4Cl (sat'd)
  2. additionpoured into water
  3. extractionThe whole was extracted with CH2Cl2 (×3)
  4. washwere washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-6e91d0a766b44814b8cf97179bf4ecef
Source dataset
uspto-grants-2010_11
Patent number
US07834063B2

Reaction notes

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