HCID 66716008, compound → [1-(4-Amino-phenyl)-1-methyl-ethyl]-carbamic acid tert-butyl ester

HRID 2271650Notes

Reaction equation

HRID 2271650 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:12])[CH3:11])=[CH:6][CH:5]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:12])[CH3:11])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 66716008HCID 66716008, compound

Product 1

HCID 68092215[1-(4-Amino-phenyl)-1-methyl-ethyl]-carbamic acid tert-butyl esterYield 36.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A pressure flask was charged with a suspension of tert-butyl 2-(4-nitrophenyl)propan-2-yl-carbamate (4.62 mmol) in ethanol (20 mL) and palladium on carbon (100 mg). The flask was placed on a Parr shaker, purged with H2 (30 psi), and stirred overnight. The crude product was filtered through celite, concentrated, and chromatographed (hexane:ethyl acetate) to obtain the desired product (420 mg, 36% over two steps) as an orange-red oil: 1H NMR (300 MHz, CDCl3) δ 7.26-7.17 (m, 2H), 6.67-6.62 (m, 2H), 4.82 (s, 1H), 1.60 (s, 3H), 1.57 (s, 3H), 1.37 (s, 9H).

Workup

  1. custompurged with H2 (30 psi)
  2. filtrationThe crude product was filtered through celite,
  3. concentrationconcentrated
  4. customchromatographed (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-f61a51418af2495b91b17423fdbe6791
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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