Sodium borohydride → HCID 70189103, compound

HRID 2269393Notes

Reaction equation

HRID 2269393 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[CH:11]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[NH:12][C@H:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:14].[BH4-].[Na+]>O.O.O.O.O.O.[Ni](Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[CH:11]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[NH:12][C@H:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:14]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 70189727HCID 70189727, compound

Product 1

HCID 70189103HCID 70189103, compound

Reagents, catalysts & solvents 1

HCID 11791229Dichloronickel;hexahydrateCatalyst

Procedure

In a similar manner to that described in Example (1b), N-[(2-chloro-5-nitrophenyl)phenylmethyl]-N-[(S)-1-phenylethyl]amine (2.58 g) [prepared as described in step (a) above], nickel chloride hexahydrate (3.33 g) and sodium borohydride (1.06 g) were reacted. The crude product was separated and purified by chromatography through a silica gel column using a 1:10 by volume mixture of ethyl acetate and toluene as the eluant, to afford isomer A (771 mg) as a colorless oil and isomer B (659 mg) as a pale yellow oil of the title compound.

Workup

  1. customwere reacted
  2. customThe crude product was separated
  3. custompurified by chromatography through a silica gel column
  4. additionby volume mixture of ethyl acetate and toluene as the eluant

Sources & evidence

ORD record
ord-111362b02af6488fae48f024bb264e56
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

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