Triethylamine → HCID 59262121, compound

HRID 534748Notes

Reaction equation

HRID 534748 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[CH2:11][N:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@@H:14]([CH3:25])[CH2:13]1.C(N(CC)CC)C>CO.[Pt]>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([CH2:11][N:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[C@@H:14]([CH3:25])[CH2:13]2)=[C:2]([F:1])[CH:7]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 59262143HCID 59262143, compound

Product 1

HCID 59262121HCID 59262121, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

1,1-Dimethylethyl (2S)-4-[(2-fluoro-4-nitrophenyl)methyl]-2-methyl-1-piperazinecarboxylate (D65) (2.05 g, 5.801 mmol) was taken up in methanol (50 mL) and wet (50% w/w water) 5% platinum on carbon (2 g) and triethylamine (8 mL, 58.01 mmol) were added. The mixture was hydrogenated at atmospheric pressure and room temperature for 2.5-3 h. The mixture was filtered and the filtrate concentrated to give the crude product which was purified by column chromatography. Elution with EtOAc/pentane yielded the title compound as an almost colourless gum (1.15 g). δH (CDCl3, 400 MHz) 7.11 (1H, t), 6.42 (1H, dd), 6.35 (1H, dd), 4.17 (1H, br.s), 3.79 (1H, d), 3.72 (2H, s), 3.43 (2H, m), 3.07 (1H, td), 2.74 (1H, m), 2.58 (1H, d), 2.14 (1H, dd), 1.99 (1H, m), 1.45 (9H, s), 1.20 (3H, d).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated
  3. customto give the crude product which
  4. customwas purified by column chromatography
  5. washElution with EtOAc/pentane

Sources & evidence

ORD record
ord-9cf8ec4a69e84173bc3d3732b77c9f9d
Source dataset
uspto-grants-2014_10
Patent number
US08853218B2

Reaction notes

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