(S)-2-(2-Bromo-6-methyl-4-nitrophenyl)-2-tert-butoxyethyl pivalate → (S)-2-(4-amino-2-bromo-6-methylphenyl)-2-tert-butoxyethyl pivalate

HRID 879272Notes

Reaction equation

HRID 879272 reaction equation
[C:1]([O:7][CH2:8][C@H:9]([C:15]1[C:20]([CH3:21])=[CH:19][C:18]([N+:22]([O-])=O)=[CH:17][C:16]=1[Br:25])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]>CCO.CCOC(C)=O.[Pt]>[C:1]([O:7][CH2:8][C@H:9]([C:15]1[C:20]([CH3:21])=[CH:19][C:18]([NH2:22])=[CH:17][C:16]=1[Br:25])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])(=[O:6])[C:2]([CH3:3])([CH3:4])[CH3:5]

Participants

5

Reactant 1

HCID 70981268(S)-2-(2-Bromo-6-methyl-4-nitrophenyl)-2-tert-butoxyethyl pivalate

Product 1

HCID 86699788(S)-2-(4-amino-2-bromo-6-methylphenyl)-2-tert-butoxyethyl pivalateYield 82.4%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-2-(2-Bromo-6-methyl-4-nitrophenyl)-2-tert-butoxyethyl pivalate (9 g, 0.022 mol) in EtOH (50 mL) and EtOAc (50 mL) was added Pt/C (1.4 g), and the reaction was fitted with a balloon of H2. The reaction mixture was stirred at room temperature for 3 h. TLC showed the reaction was complete. The reaction mixture was filtered over Celite. The filtrate was concentrated in vacuo to give (S)-2-(4-amino-2-bromo-6-methylphenyl)-2-tert-butoxyethyl pivalate (7 g, 82%) as brown oil, which was immediately used for next step without further purification. 1H-NMR: 400 MHz, (CDCl3) δ: 6.70 (s, 1H), 6.40 (s, 1H), 5.38 (app. s, broad, 1H), 4.22 (app. s, broad, 1H), 4.05 (app. s, broad, 1H), 3.60 (app. s, broad, 2H), 2.47 (s, 3H), 1.17 (s, 9H), 1.13 (s, 9H).

Workup

  1. customthe reaction was fitted with a balloon of H2
  2. filtrationThe reaction mixture was filtered over Celite
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-881cc51598834860a425b96f12ca4756
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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