Sodium borohydride → 3-{[(R)-1-(3,5-Difluorophenyl)ethylamino]-(4-fluorophenyl)methyl}phenylamine

HRID 2269457Notes

Reaction equation

HRID 2269457 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:9]([NH:11][CH:12]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-])=O)[CH:14]=2)[CH3:10])[CH:5]=[C:6]([F:8])[CH:7]=1.[BH4-].[Na+]>O.O.O.O.O.O.[Ni](Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([C@H:9]([NH:11][CH:12]([C:22]2[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=2)[C:13]2[CH:14]=[C:15]([NH2:19])[CH:16]=[CH:17][CH:18]=2)[CH3:10])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 70189758N-[(R)-1-(3,5-Difluorophenyl)ethyl]-N-[(4-fluorophenyl)-(3-nitrophenyl)methyl]amine

Product 1

HCID 701897683-{[(R)-1-(3,5-Difluorophenyl)ethylamino]-(4-fluorophenyl)methyl}phenylamine

Reagents, catalysts & solvents 1

HCID 11791229Dichloronickel;hexahydrateCatalyst

Procedure

Following a reaction and purification procedure similar to those described in Example (59b), 4.40 g of N-[(R)-1-(3,5-difluorophenyl)ethyl]-N-[(4-fluorophenyl)-(3-nitrophenyl)methyl]amine [prepared as described in step (a) above], 6.54 g of nickel chloride hexahydrate and 1.81 g of sodium borohydride were reacted, to obtain 1.24 g of isomer A and 1.66 g of isomer B of the title compound as yellow oils, respectively.

Workup

  1. customa reaction and purification procedure similar to
  2. customwere reacted

Sources & evidence

ORD record
ord-5cc33074077446558967c770e935ac58
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

Loading…