Lithium borohydride → HCID 68765311, compound

HRID 1628434Notes

Reaction equation

HRID 1628434 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([NH:11][C:12]3[C:20]4[O:19][C:18]([F:22])([F:21])[O:17][C:16]=4[CH:15]=[CH:14][CH:13]=3)[N:7]([CH2:23][CH2:24][CH2:25][C:26](OCC)=[O:27])[C:6]=2[C:5]([CH:31]([CH2:34][CH3:35])[CH2:32][CH3:33])=[CH:4][CH:3]=1.[BH4-].[Li+]>O1CCCC1>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([NH:11][C:12]3[C:20]4[O:19][C:18]([F:22])([F:21])[O:17][C:16]=4[CH:15]=[CH:14][CH:13]=3)[N:7]([CH2:23][CH2:24][CH2:25][CH2:26][OH:27])[C:6]=2[C:5]([CH:31]([CH2:34][CH3:35])[CH2:32][CH3:33])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 68765177HCID 68765177, compound

Product 1

HCID 68765311HCID 68765311, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-[4-chloro-2-[(2,2-difluoro-1,3-benzodioxol-4-yl)amino]-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]butanoate (900 mg, 1.77 mmol) in tetrahydrofuran (8.0 mL) was added lithium tetrahydroborate (193 mg, 8.86 mmol) at 0° C. The mixture was stirred at room temperature for 19 hr. and the reaction was quenched by methanol. The mixture was neutralized with aqueous saturated ammonium chloride, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 15-50% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the solid, which was washed with n-hexane to give the title compound as a colorless powder (630 mg, 1.35 mmol, 76%).

Workup

  1. customand the reaction was quenched by methanol
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel eluting with a 15-50% ethyl acetate/n-hexane gradient mixture
  8. concentrationThe filtrate was concentrated in vacuo
  9. customto give the solid, which
  10. washwas washed with n-hexane

Sources & evidence

ORD record
ord-a5b917bf1aa241dbb1015fa6a4fe52ae
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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