Sodium borohydride → HCID 67359952, compound

HRID 1668395Notes

Reaction equation

HRID 1668395 reaction equation
[C:1]([N:4]([CH3:22])[N:5]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]#[N:21])=[CH:15][CH:14]=1)[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])(=[O:3])[CH3:2].[BH4-].[Na+]>CO.C(OCC)(=O)C.[Co](Cl)Cl>[C:1]([N:4]([CH3:22])[N:5]([C:13]1[CH:14]=[CH:15][C:16]([CH2:19][CH2:20][NH2:21])=[CH:17][CH:18]=1)[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 67359758HCID 67359758, compound

Product 1

HCID 67359952HCID 67359952, compound

Reagents, catalysts & solvents 3

HCID 24288Cobalt(II) chlorideCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 2-acetyl-1-[4-(cyanomethyl)phenyl]-2-methylhydrazinecarboxylate (607 mg) and cobalt chloride (520 mg) were dissolved in methanol (20 ml), and sodium borohydride (757 mg) was added by small portions at 0° C. The reaction mixture was stirred at room temperature for 2.5 hr, and diluted with ethyl acetate (200 ml). The obtained diluted solution was passed through basic silica gel (100 g) and washed with ethyl acetate:methanol=10:1 (volume ratio). The filtrate was concentrated under reduced pressure to give tert-butyl 2-acetyl-1-[4-(2-aminoethyl)phenyl]-2-methylhydrazinecarboxylate as a colorless oil.

Workup

  1. washwashed with ethyl acetate
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0d518ca08e854d4b9f1711e9939c4883
Source dataset
uspto-grants-2011_08
Patent number
US07989445B2

Reaction notes

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