Sodium borohydride → HCID 59410109, compound

HRID 1915482Notes

Reaction equation

HRID 1915482 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([N+:15]([O-])=O)[C:12]([C:18]([F:21])([F:20])[F:19])=[CH:11][C:10]=1[CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO.Cl[Ni]Cl>[CH2:1]([O:8][C:9]1[C:10]([CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:11][C:12]([C:18]([F:21])([F:19])[F:20])=[C:13]([CH:14]=1)[NH2:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 59410074HCID 59410074, compound

Product 1

HCID 59410109HCID 59410109, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-(benzyloxy)-2-cyclohexyl-5-nitro-4-(trifluoromethyl)benzene (250 mg, 0.66 mmol) and NiCl2 (170 mg, 1.31 mmol) in methanol (2.5 mL) was added NaBH4 (50 mg, 1.32 mmol) portionwise at 0° C. The reaction mixture turned black after 5 minutes. The reaction mixture was quenched with NaHCO3 and diluted with EtOAc. The reaction mixture was filtered through a plug of celite, the layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layer was dried over Na2SO4, filtered and concentrated. The residue was then purified by silica gel column chromatography using 10% EtOAc/hexane gradient to give 5-benzyloxy-4-cyclohexyl-2-(trifluoromethyl)aniline (150 mg, 65%). LC/MS: m/z 350.3 (M+H)+ at 2.40 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customThe reaction mixture was quenched with NaHCO3
  2. additiondiluted with EtOAc
  3. filtrationThe reaction mixture was filtered through a plug of celite
  4. customthe layers were separated
  5. extractionthe aqueous layer was extracted with EtOAc
  6. dry with materialThe combined organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9f24e82b4de8450d81cf0e8e304a3a05
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Reaction notes

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