Sodium borohydride → 2-Amino-alpha-(3-chlorophenyl)-5-[2-(4-chlorophenyl)-1,3-dioxolan-2-yl]-benzenemethanol

HRID 860783

Reaction equation

HRID 860783 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[O:12][CH2:11][CH2:10][O:9]2)=[CH:4][C:3]=1[C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=1)=[O:21].[BH4-].[Na+]>CO.C1COCC1>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:13]3[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=3)[O:12][CH2:11][CH2:10][O:9]2)=[CH:4][C:3]=1[CH:20]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=1)[OH:21]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 22626605[2-Amino-5-[2-(4-chlorophenyl)-1,3-dioxolan-2-yl]phenyl](3-chlorophenyl)methanone

Product 1

HCID 690198082-Amino-alpha-(3-chlorophenyl)-5-[2-(4-chlorophenyl)-1,3-dioxolan-2-yl]-benzenemethanolYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of [2-amino-5-[2-(4-chlorophenyl)-1,3-dioxolan-2-yl]phenyl](3-chlorophenyl)methanone (prepared as described in WO 98/49157) (0.088 mol) in methanol (300 ml) and THF (100 ml) was cooled on an ice bath. sodium tetrahydroborate (0.088 mol) was added portionwise. The mixture was stirred at a low temperature for 30 min, then hydrolized and extracted with DCM. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated till dryness. The product was used without further purification, yielding 36.6 g (100%) of 2-amino-α-(3-chlorophenyl)-5-[2-(4-chlorophenyl)-1,3-dioxolan-2-yl]-benzenemethanol (intermediate 9).

Workup

  1. temperaturewas cooled on an ice bath
  2. extractionhydrolized and extracted with DCM
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated till dryness
  7. customThe product was used without further purification

Sources & evidence

ORD record
ord-233094ed9755435cbac414678207f1cd
Source dataset
uspto-grants-2006_12
Patent number
US07153958B2

Linked notes

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