Ethyl Acetate → (1R,2R)-2-(4-aminophenyl)cyclopropane-1-carboxylic acid

HRID 1173036Notes

Reaction equation

HRID 1173036 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]2[CH2:12][C@H:11]2[C:13]([OH:15])=[O:14])=[CH:6][CH:5]=1)([O-])=O.C(OCC)(=O)C>O=[Pt]=O.CO>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C@@H:10]2[CH2:12][C@H:11]2[C:13]([OH:15])=[O:14])=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 12854631rac-(1R,2R)-2-(4-nitrophenyl)cyclopropane-1-carboxylic acid

Product 1

HCID 68668314(1R,2R)-2-(4-aminophenyl)cyclopropane-1-carboxylic acidYield 101.8%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A Fischer-Porter bottle containing racemic-(trans)-2-(4-nitrophenyl)cyclopropanecarboxylic acid (V-2) (4.60 g, 22.22 mmol), PtO2 (0.16 g, 0.70 mmol), ethyl acetate (70 mL) and MeOH (50 mL) was purged with N2 (3x's) then charged with 40 psig H2 at RT. After 1 h, the bottle was carefully vented and the suspension was filtered through Celite. The solution was concentrated to give the title compound as a white powder (4.01 g, ˜100%). 1H NMR (400 MHz, DMSO) δ 6.79 (d, J=8.6 Hz, 2H), 6.47 (d, J=8.6, 2H), 5.02 (bs, 2H), 2.21-2.16 (m, 1H), 1.61-1.56 (m, 1H), 1.31-1.28 (m, 1H), 1.19-1.14 (m, 1H). ES-MS m/z 176.3 (MH−).

Workup

  1. customwas purged with N2 (3x's)
  2. additionthen charged with 40 psig H2 at RT
  3. filtrationthe suspension was filtered through Celite
  4. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-dff2ec8c227b48fb8cf2f06f94aee408
Source dataset
uspto-grants-2010_11
Patent number
US07834013B2

Reaction notes

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