Lithium borohydride → HCID 58386143, compound

HRID 1963023Notes

Reaction equation

HRID 1963023 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:10]([C:18](OCC3C=CC=CC=3)=[O:19])=[N:9]2)=[CH:4][CH:3]=1.[Li+].[BH4-]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:10]([CH2:18][OH:19])=[N:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 58386115HCID 58386115, compound

Product 1

HCID 58386143HCID 58386143, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-benzyl 4-ethyl 1-(4-chlorophenyl)-1H-pyrazole-3,4-dicarboxylate (Example 1C, 3.57 g, 9.28 mmol) in THF (100 mL) was added LiBH4 solution (7.89 mL, 15.77 mmol, 2M in THF). The reaction mixture was stirred at room temperature for 5 h. The resulting mixture was quenched with aqueous sat. NH4Cl solution (10 mL). Solvent was evaporated and the crude product was diluted with H2O (30 mL), extracted with EtOAc (150 mL). The organic layer was separated, dried over MgSO4 and concentrated to give a crude product which was further purified by ISCO automated chromatography (42 g, Hexane/EtOAc, 100:0 to 60:40 gradient) to give the product as a white solid (1.5 g, 58% yield). 1H NMR (CDCl3) δ 1.40 (t, J=7.2 Hz, 3H), 4.38 (q, J=7.2 Hz, 2H), 3.98 (t, J=7.1 Hz, 1H). 4.88 (d, 7.1 Hz, 2H), 7.40-7.48 (m, 2H), 7.60-7.67 (m, 2H), 8.32 (s, 1H). LC-MS, [M+H]+=281.0.

Workup

  1. customThe resulting mixture was quenched with aqueous sat. NH4Cl solution (10 mL)
  2. customSolvent was evaporated
  3. additionthe crude product was diluted with H2O (30 mL)
  4. extractionextracted with EtOAc (150 mL)
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customto give a crude product which
  9. customwas further purified by ISCO automated chromatography (42 g, Hexane/EtOAc, 100:0 to 60:40 gradient)

Sources & evidence

ORD record
ord-1388a1aa69bf4f5ba6d975653d453da7
Source dataset
uspto-grants-2013_04
Patent number
US08415386B2

Reaction notes

Loading…