4-Tert-butyl-2-cyclopentenyl-5-nitrophenyl methyl carbonate → 5-Amino-4-tert-butyl-2-cyclopentylphenyl methyl carbonate

HRID 1465084Notes

Reaction equation

HRID 1465084 reaction equation
[C:1](=[O:23])([O:21][CH3:22])[O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[C:6]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:5][C:4]=1[C:16]1[CH2:20][CH2:19][CH2:18][CH:17]=1>C(O)C.[Pd]>[C:1](=[O:23])([O:21][CH3:22])[O:2][C:3]1[CH:8]=[C:7]([NH2:9])[C:6]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:5][C:4]=1[CH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

4

Reactant 1

HCID 593950444-Tert-butyl-2-cyclopentenyl-5-nitrophenyl methyl carbonate

Product 1

HCID 593950265-Amino-4-tert-butyl-2-cyclopentylphenyl methyl carbonateYield 92.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a flask charged with 10% Pd/C (132 mg) under inert atmosphere was added a solution of 4-tert-butyl-2-cyclopentenyl-5-nitrophenyl methyl carbonate (660 mg, 2.07 mmol) in ethanol (20 mL). The reaction was stirred under H2 atmosphere for 3 h, then filtered and dried down to provide 5-amino-4-tert-butyl-2-cyclopentylphenyl methyl carbonate as an off-white crystalline solid (556 mg, 92% yield). 1H NMR (400.0 MHz, DMSO-d6) δ 6.97 (s, 1H), 6.38 (s, 1H), 4.81 (s, 2H), 3.80 (s, 3H), 2.84 (m, 1H), 1.87-1.80 (m, 2H), 1.72-1.66 (m, 2H), 1.62-1.56 (m, 2H), 1.47-1.39 (m, 2H), 1.32 (s, 9H).

Workup

  1. filtrationfiltered
  2. customdried down

Sources & evidence

ORD record
ord-f6213c2c3a16405bafe0c8d260114fcc
Source dataset
uspto-grants-2015_04
Patent number
US08999976B2

Reaction notes

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