HCID 69893528, compound → HCID 69892414, compound

HRID 2415050Notes

Reaction equation

HRID 2415050 reaction equation
C[O:2][C:3](=O)[C@@H:4]1[CH2:8][CH2:7][C:6](=[CH:9][N+:10]([O-])=O)[N:5]1[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[H][H]>[Pd].CO>[CH2:13]([N:5]1[C@@H:6]2[CH2:7][CH2:8][C@H:4]1[C:3](=[O:2])[NH:10][CH2:9]2)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 69893528HCID 69893528, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69892414HCID 69892414, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(S)-1-Benzyl-5-nitromethylene proline methyl ester (3.22 g, 11.6 mmol) was added to a suspension of 10% palladium on carbon (1.35 g) in methanol (75 mL) and the mixture was hydrogenated under 30 psi of hydrogen for 20 h. The catalyst was removed by filtration through a pad of celite and the solvent was removed under reduced pressure. The crude product was purified by silica gel chromatography, eluting with 5% methanol/methylene chloride, to yield the desired product (1.49 g, 60%). 1H NMR (300 MHz, CDCl3): δ 1.78 (m, 1 H), 2.08 (m, 1 H), 2.22 (m, 2 H), 2.99 (dd, 1 H, J=2.0, 11.3), 3.38 (m, 1 H), 3.49 (d, 1 H, J=6.1), 3.67 (dd, 1 H, J=3.9, 11.3), 3.78 (s, 2 H), 5.66 (s, 1 H), 7.33 (m, 5 H). MS ESI+: m/z 217 (M+H)+.

Workup

  1. customThe catalyst was removed by filtration through a pad of celite
  2. customthe solvent was removed under reduced pressure
  3. customThe crude product was purified by silica gel chromatography
  4. washeluting with 5% methanol/methylene chloride

Sources & evidence

ORD record
ord-5dc7710149ae4b9a9571fabe151e13dc
Source dataset
uspto-grants-2004_11
Patent number
US06818643B1

Reaction notes

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