Formaldehyde → 4-hydroxy-N-methylproline

HRID 2396691Notes

Reaction equation

HRID 2396691 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.[H][H]>[Pd].O.CO>[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

7

Reactant 3

HCID 712FormaldehydeHCID 5810L-HydroxyprolineHCID 178418361HCID 178418361, compound

Product 1

HCID 117687004-hydroxy-N-methylproline

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A suspension of 10% palladium on carbon in water (25 ml) was added to a suspension of trans-4-hydroxy-L-proline (6.576 g., 50.10 mmol) in methanol (100 ml) and 37% aqueous formaldehyde (16 ml, 213.5 mmol) in a Parr bottle. The bottle was pressurized to 50 psi with hydrogen and shaken overnight. The catalyst was removed by filtration through a pad of celite which was washed thoroughly with methanol (100 ml). Evaporation of the methanol and excess formaldehyde yielded N-methyl-trans-4-hydroxy-L-proline as a white solid which was recrystallized from methanol/diethyl ether to give 6.425 g. of white needles, m.p. 236°-238 ° (decomposition with gas evolution).

Workup

  1. customThe catalyst was removed by filtration through a pad of celite which
  2. washwas washed thoroughly with methanol (100 ml)
  3. customEvaporation of the methanol and excess formaldehyde

Sources & evidence

ORD record
ord-43cf2f39754240258b653b4bf00c51ac
Source dataset
uspto-grants-1996_02
Patent number
US05494898

Reaction notes

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