Sodium borohydride → HCID 70189163, compound

HRID 2269398Notes

Reaction equation

HRID 2269398 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[NH:11][C@H:12]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[C:16]([F:21])[CH:15]=2)[CH3:13])[CH:7]=[CH:8][CH:9]=1)([O-])=O.[BH4-].[Na+]>CO.O.O.O.O.O.O.[Ni](Cl)Cl>[CH3:29][O:28][C:25]1[CH:26]=[CH:27][C:22]([CH:10]([NH:11][C@H:12]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[C:16]([F:21])[CH:15]=2)[CH3:13])[C:6]2[CH:5]=[C:4]([NH2:1])[CH:9]=[CH:8][CH:7]=2)=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 70189780HCID 70189780, compound

Product 1

HCID 70189163HCID 70189163, compound

Reagents, catalysts & solvents 2

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 887MethanolSolvent

Procedure

In a similar manner to that described in Example (1b), a solution N-[(3-nitrophenyl)-(4-methoxyphenyl)methyl]-[(S)-1-(3,4-difluorophenyl)ethyl]amine (1.50 g) [prepared as described in step (a) above] in methanol (50 ml), nickel chloride hexahydrate (1.79 g) and sodium borohydride (600 mg) were reacted, and the reaction mixture was purified by chromatography through a silica gel column using a 1:8 by volume mixture of ethyl acetate and toluene as the eluant, to afford isomer A (199 mg) as a yellow oil and isomer B (290 mg) as a yellow oil of the title compound.

Workup

  1. customthe reaction mixture was purified by chromatography through a silica gel column
  2. additionby volume mixture of ethyl acetate and toluene as the eluant

Sources & evidence

ORD record
ord-2ea5cb511def470a989f7fd56620e3e0
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

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