Formaldehyde → 1,2-Dimethyl-L-proline

HRID 74793Notes

Reaction equation

HRID 74793 reaction equation
[CH3:1][C@@:2]1([C:7]([OH:9])=[O:8])[CH2:6][CH2:5][CH2:4][NH:3]1.[CH2:10]=O.O.[H][H]>[Pd].CO>[CH3:10][N:3]1[CH2:4][CH2:5][CH2:6][C@@:2]1([CH3:1])[C:7]([OH:9])=[O:8]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 69936642-Methyl-L-prolineHCID 178418361HCID 178418361, compound

Product 1

HCID 533022611,2-Dimethyl-L-prolineYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A parr flask containing 2-methyl-L-proline (1.0 g, 7.7 mmol, 1.0 eq.), 40 mL of methanol, Formaldehyde 37 wt. % in water (2.1 mL, 77 mmol, 10 eq.), and Palladium 10 wt. % on Carbon (313 mg, 2.94 mmol, 0.38 eq.) was placed on a parr shaker and allowed to shake under 40 psi of hydrogen for -12 hours. Hydrogen was removed and the reaction was filtered through a pad of celite which was rinsed with a solution of 50% methanol 50% dichloromethane. Residue was concentrated in vacuo yielding #150 (1.1 g, 100%) as a white slight black colored solid. LC-MS (Protocol Q): m/z 144.0 [M+H+] retention time=0.17 minutes.

Workup

  1. customHydrogen was removed
  2. filtrationthe reaction was filtered through a pad of celite which
  3. washwas rinsed with a solution of 50% methanol 50% dichloromethane
  4. concentrationResidue was concentrated in vacuo

Sources & evidence

ORD record
ord-fbc4f10ead2d4ac69bcbe4d3a3cc4f83
Source dataset
uspto-grants-2014_09
Patent number
US08828401B2

Reaction notes

Loading…