Formaldehyde → 4-hydroxy-N-methylproline

HRID 466749Notes

Reaction equation

HRID 466749 reaction equation
[OH:1][C@H:2]1[CH2:6][NH:5][C@H:4]([C:7]([OH:9])=[O:8])[CH2:3]1.[CH2:10]=O>O.[Pd]>[CH3:10][N:5]1[CH2:6][C@H:2]([OH:1])[CH2:3][C@H:4]1[C:7]([OH:9])=[O:8]

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 5810L-Hydroxyproline

Product 1

HCID 117687004-hydroxy-N-methylprolineYield 98.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

To 40 g (305 mmol) of trans-4-hydroxy-L-proline in 80 ml of water was added 80 ml of 30% aqueous formaldehyde solution and 7.0 g of 5% palladium on carbon catalyst (50% wet), and the mixture was hydrogenated at 50 psig using a Parr Shaker. After 24 hours, the catalyst was recovered by filtration over diatomaceous earth and the filtrate evaporated under reduced pressure to provide 43.5 g (98.3%) of title product mp 140°-142° C. (decomposition); 1H-NMR (D2O): 4.65 (m, 1H), 4.20 (dd, 1H), 3.97 (dd, 1H), 3.2 (dm, 1H), 2.50 (m, 1H), 2.25 (m, 1H); [alpha]D =-54.8° (c=1.18, H2O).

Workup

  1. filtrationthe catalyst was recovered by filtration over diatomaceous earth
  2. customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-d669b30a409444f58fc08fd9d65cd320
Source dataset
uspto-grants-1992_10
Patent number
US05157125

Reaction notes

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