Sodium borohydride → HCID 69023059, compound

HRID 860790Notes

Reaction equation

HRID 860790 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[C:9]2[N:13]([CH3:14])[CH:12]=[N:11][CH:10]=2)=[CH:4][C:3]=1[C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=1)=[O:23].[BH4-].[Na+]>CO>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=2)[C:9]2[N:13]([CH3:14])[CH:12]=[N:11][CH:10]=2)=[CH:4][C:3]=1[CH:22]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=1)[OH:23]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 69023509HCID 69023509, compound

Product 1

HCID 69023059HCID 69023059, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of intermediate (16) (0.0848 mol) in methanol (400 ml) was cooled to 10° C. sodium tetrahydroborate (0.102 mol) was added portionwise. The mixture was stirred at room temperature for 2 hours, poured out into ice water and extracted with DCM. The organic layer was separated, washed with water, dried (MgSO4), filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 95/5/0.1; 20–45 μm). The pure fractions were collected and the solvent was evaporated, yielding 12.3 g (33%) of 2-amino-α-(3-chlorophenyl)-5-[(4-chlorophenyl)(1-methyl-1H-imidazol-5-yl)methyl]-benzenemethanol (intermediate 17).

Workup

  1. additionwas added portionwise
  2. extractionextracted with DCM
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 95/5/0.1; 20–45 μm)
  9. customThe pure fractions were collected
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-2da3bc96b94f48fd84f7bc40a55f0a67
Source dataset
uspto-grants-2006_12
Patent number
US07153958B2

Reaction notes

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