4-Pyridinemethanamine → (S)-1-Methoxy-3-(pyridin-4-ylmethylamino)propan-2-ol

HRID 2092032Notes

Reaction equation

HRID 2092032 reaction equation
[CH3:1][O:2][CH2:3][C@@H:4]1[O:6][CH2:5]1.[N:7]1[CH:12]=[CH:11][C:10]([CH2:13][NH2:14])=[CH:9][CH:8]=1>CO>[CH3:1][O:2][CH2:3][C@@H:4]([OH:6])[CH2:5][NH:14][CH2:13][C:10]1[CH:11]=[CH:12][N:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 773174-PyridinemethanamineHCID 2734441(2R)-2-(Methoxymethyl)oxirane

Product 1

HCID 59574413(S)-1-Methoxy-3-(pyridin-4-ylmethylamino)propan-2-olYield 17%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

(R)-(−)-Glycidyl methyl ether (88 mg, 1 mmol) and 4-picolylamine (108 mg, 1 mmol) in methanol (1 mL) were sealed in a reaction tube and heated at 120° C. for 30 minutes with stirring and microwave irradiation. The solvent was removed by vacuum distillation. The resulting residue was purified by silica gel column chromatography (ethyl acetate) to give the desired product (17% yield).

Workup

  1. custommicrowave irradiation
  2. customThe solvent was removed by vacuum distillation
  3. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-b3ea38495ad7475f82fda0a7f9e8f9aa
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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