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

HRID 2269449Notes

Reaction equation

HRID 2269449 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]([O:28][CH3:29])=[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]([O:28][CH3:29])=[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 70189169N-[(R)-1-(3,5-Difluorophenyl)ethyl]-N-[(4-methoxyphenyl)-(3-nitrophenyl)methyl]amine

Product 1

HCID 701893053-{[(R)-1-(3,5-Difluorophenyl)ethylamino]-(4-methoxyphenyl)methyl}phenylamine

Reagents, catalysts & solvents 1

HCID 11791229Dichloronickel;hexahydrateCatalyst

Procedure

Following a similar procedure to that described in Example (1b), 820 mg of isomer B of N-[(R)-1-(3,5-difluorophenyl)ethyl]-N-[(4-methoxyphenyl)-(3-nitrophenyl)methyl]amine [prepared as described in step (a) above], 1.13 g of nickel chloride hexahydrate and 328 mg of sodium borohydride were reacted, to obtain 480 mg of isomer B of the title compound as a yellow oil.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-2748c1b6f1624c2aa0aabcabf106edd7
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

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