1,1-Dimethylethyl 4-(hydroxyimino)-4-phenylbutylcarbamate → tert-butyl N-(4-amino-4-phenylbutyl)carbamate

HRID 352112Notes

Reaction equation

HRID 352112 reaction equation
O[N:2]=[C:3]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11]>C(O)C.[Pd]>[NH2:2][CH:3]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:11])[CH3:12]

Participants

4

Reactant 1

HCID 739931561,1-Dimethylethyl 4-(hydroxyimino)-4-phenylbutylcarbamate

Product 1

HCID 16795070tert-butyl N-(4-amino-4-phenylbutyl)carbamateYield 107.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1,1-Dimethylethyl 4-(hydroxyimino)-4-phenylbutylcarbamate (2.3 g, 8.3 mmol), in absolute ethanol was hydrogenated over 10% palladium on charcoal (0.5 g) at 5 bar pressure for 20 h. The mixture was then filtered and the filtrate concentrated to dryness to afford the title compound as a colourless oil (2.36 g).

Workup

  1. filtrationThe mixture was then filtered
  2. concentrationthe filtrate concentrated to dryness

Sources & evidence

ORD record
ord-67fc204a87ee4cd9ade8e6b1f0e75ae7
Source dataset
uspto-grants-2004_06
Patent number
US06743939B2

Reaction notes

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