HCID 20725687, compound → HCID 20725689, compound

HRID 1582344Notes

Reaction equation

HRID 1582344 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:21]([O-])=O)[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:12][CH2:11][C@H:10]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]1>C(OCC)(=O)C.[Pd]>[NH2:21][C:4]1[CH:5]=[CH:6][C:7]([N:8]2[CH2:12][CH2:11][C@H:10]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]2)=[C:2]([F:1])[CH:3]=1

Participants

4

Reactant 1

HCID 20725687HCID 20725687, compound

Product 1

HCID 20725689HCID 20725689, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3-Fluoro-4-(3(S)-(t-butoxycarbonyl)aminopyrrolidin-1-yl)nitrobenzene (33.5 g, 0.103 M) was dissolved in ethyl acetate (500 ml) treated with palladium catalyst (10% on carbon, 5 g) and hydrogenated at atmospheric pressure until the theoretical uptake of gas. After filtration through celite and evaporation, the required product was obtained as a red gum of sufficient quality for use without purification (30.4 g). NMR (DMSO-d6) δ: 1.35 (s, 9H); 1.71 (m, 1H); 2.06 (m, 1H); 2.87 (dd, 1H); 3.05 (m, 1H); 3.11 (m, 1H); 3.26 (m overlapping H2O, ˜1H); 3.97 (m, 1H); 4.68 (s, 2H); 6.25 (dd, 1H); 6.31 (dd, 1H); 6.51 (t, 1H); 7.03 (d, 1H). MS (ESP): 296 (MH+) for C15H22FN3O2

Workup

  1. filtrationAfter filtration
  2. customthrough celite and evaporation

Sources & evidence

ORD record
ord-9077125d18dd4f66b2529a286d1ba125
Source dataset
uspto-grants-2004_05
Patent number
US06734200B1

Reaction notes

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