Acetic Acid → HCID 23533963, compound

HRID 2373691Notes

Reaction equation

HRID 2373691 reaction equation
[C:1]([O:5][C:6](=[O:21])[N:7]([CH:18]([CH3:20])[CH3:19])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-])=O)([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C>C(OCC)(=O)C.[Pd]>[C:1]([O:5][C:6](=[O:21])[N:7]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH2:15])[CH:18]([CH3:20])[CH3:19])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 23533965HCID 23533965, compound

Product 1

HCID 23533963HCID 23533963, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of isopropyl-(2-nitro-benzyl)-carbamic acid tert-butyl ester (730 mg, 2.48 mmol) in ethyl acetate (10 ml) was added acetic acid (0.156 ml, 2,73 mmol) and catalytic amount of palladium 10 wt. % on activated carbon. The mixture was stirred overnight under hydrogen atmosphere. The mixture was filtered and concentrated in vacuo. The residue was purified by column chromatography (15% ethyl acetate-hexane) to afford (2-amino-benzyl)-isopropyl-carbamic acid tert-butyl ester (f) (568 mg, 2.15 mmol, 87%) as reddish oil.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by column chromatography (15% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-eab76b5d51b14d2c8e1ef5d1b5f78ddc
Source dataset
uspto-grants-2008_12
Patent number
US07459561B2

Reaction notes

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