Sodium borohydride → HCID 70188108, compound

HRID 2269407Notes

Reaction equation

HRID 2269407 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[O:27][CH3:28])[NH:11][C@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[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>[CH3:28][O:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[CH:10]([NH:11][C@H:12]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1)[CH3:13])[C:6]1[CH:5]=[C:4]([NH2:1])[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 70188163HCID 70188163, compound

Product 1

HCID 70188108HCID 70188108, compoundYield 29.3%

Reagents, catalysts & solvents 2

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 887MethanolSolvent

Procedure

In a similar manner to that described in Example (1b), a solution of N-[(3-nitrophenyl)-(2-methoxyphenyl)methyl]-N-[(S)-1-(3-fluorophenyl)ethyl]amine (2.96 g) [prepared as described in step (a) above] in methanol (50 ml), nickel chloride hexahydrate (3.70 g) and sodium borohydride (1.24 g) were reacted, and the crude product was purified by reverse phase HPLC using a 40:60 by volume mixture of acetonitrile and an acetic acid buffer solution (water/acetic acid/triethylamine=1000:2:2) as the eluant, to afford isomer A of the title compound (540 mg) as a yellow oil and isomer B of the title compound (800 mg) as a yellow oil.

Workup

  1. customthe crude product was purified by reverse phase HPLC
  2. additionby volume mixture of acetonitrile

Sources & evidence

ORD record
ord-fc458c2144bf484db6b7a6ae96781ac5
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

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