Methanol → HCID 70188066, compound

HRID 2269405Notes

Reaction equation

HRID 2269405 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]([C:21]2[CH:26]=[CH:25][C:24](OC)=[CH:23][CH:22]=2)[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+].[CH3:31][OH:32]>O.O.O.O.O.O.[Ni](Cl)Cl>[CH3:31][O:32][C:23]1[CH:22]=[C:21]([CH:10]([NH:11][C@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)[CH3:13])[C:6]2[CH:5]=[C:4]([NH2:1])[CH:9]=[CH:8][CH:7]=2)[CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 70188106HCID 70188106, compound

Product 1

HCID 70188066HCID 70188066, compound

Reagents, catalysts & solvents 1

HCID 11791229Dichloronickel;hexahydrateCatalyst

Procedure

In a similar manner to that described in Example (1b), a solution of N-[(3-nitrophenyl)-(4-methoxyphenyl)methyl]-N-[(S)-1-(3-fluorophenyl)ethyl]amine (2.79 g) [prepared as described in step (a) above] in methanol (50 ml), nickel chloride hexahydrate (3 .49 g) and sodium borohydride (1.17 g) were reacted, and the residue was purified by chromatography through a silica gel column, using mixtures of toluene and ethyl acetate ranging from 8:1 to 5:1 by volume as the eluant, and reverse phase chromatographly through a Lobar column under medium pressure using a 35:65 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 (700 mg) as a yellow oil and isomer B of the title compound (220 mg) as a yellow oil.

Workup

  1. customthe residue was purified by chromatography through a silica gel column
  2. additionby volume mixture of acetonitrile

Sources & evidence

ORD record
ord-d396e6af626248189e3b0a670fa7194e
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

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