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

HRID 2269480Notes

Reaction equation

HRID 2269480 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]=[CH:6][C:7]=1[F:8].[BH4-].[Na+]>O.O.O.O.O.O.[Ni](Cl)Cl.CO>[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]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 70189099N-[(R)-1-(3,4-Difluorophenyl)ethyl]-N-[(4-fluorophenyl)-(3-nitrophenyl)methyl]amine

Product 1

HCID 701881243-{[(R)-1-(3,4-Difluorophenyl)ethylamino]-(4-fluorophenyl)methyl}-phenylamine

Reagents, catalysts & solvents 2

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 887MethanolSolvent

Procedure

Following a similar reaction, separation and purification procedure to that described in Example (59b), 18.44 g of N-[(R)-1-(3,4-difluorophenyl)ethyl]-N-[(4-fluorophenyl)-(3-nitrophenyl)methyl]amine, 22.69 g of nickel chloride hexahydrate, 7.22 g of sodium borohydride and 150 ml of methanol were reacted, to obtain 1.27 g of isomer A and 2.79 g of isomer B of the title compound, respectively, each as a pale yellow oil.

Workup

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Sources & evidence

ORD record
ord-46233c548e1640f7b45ebfe6caad483a
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

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