Methylamine → (R)-1-(pyridin-2-yl)propan-1-amine

HRID 2066038Notes

Reaction equation

HRID 2066038 reaction equation
CC(C)[C@H]([NH:6][C@@H:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)[CH2:8][CH3:9])CO.CN.I(O)(=O)(=O)=O>CO.O>[N:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C@H:7]([NH2:6])[CH2:8][CH3:9]

Participants

6

Reactant 3

HCID 6329MethylamineHCID 65185Metaperiodic acidHCID 67083760(S)-3-methyl-2-((R)-1-(pyridin-2-yl)propylamino)butan-1-ol

Product 1

HCID 28064429(R)-1-(pyridin-2-yl)propan-1-amine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of (S)-3-methyl-2-((R)-1-(pyridin-2-yl)propylamino)butan-1-ol (step 2, crude product) (40.8 mmol) in MeOH (250 ml) was added methylamine (60 ml of a 40% aqueous solution) followed by a solution of periodic acid (37.2 g, 163 mmol) in water (70 ml). The mixture was stirred at RT overnight and the resulting white solid precipitate was filtered off. The filtrate was concentrated in vacuo to remove the MeOH. The residual aqueous layer was then extracted with EtOAc. The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo. Purification of the crude product by chromatography on silica eluting with a 0-20% MeOH/DCM gradient affords the title product; [M+H}+ 137.

Workup

  1. filtrationthe resulting white solid precipitate was filtered off
  2. concentrationThe filtrate was concentrated in vacuo
  3. customto remove the MeOH
  4. extractionThe residual aqueous layer was then extracted with EtOAc
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification of the crude product by chromatography on silica eluting with a 0-20% MeOH/DCM gradient

Sources & evidence

ORD record
ord-37e39797fdde4f53b86c8877a554b44a
Source dataset
uspto-grants-2012_10
Patent number
US08288588B2

Reaction notes

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