Formic Acid → (2R)-1-[Benzyl(methyl)amino]propan-2-ol

HRID 1926908Notes

Reaction equation

HRID 1926908 reaction equation
[CH2:1]([NH:8][CH2:9][C@H:10]([OH:12])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=O.[CH:15](O)=O.[OH-].[Na+]>>[CH2:1]([N:8]([CH3:15])[CH2:9][C@H:10]([OH:12])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 284Formic AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 964915(R)-1-(Benzylamino)-2-propanol

Product 1

HCID 15005725(2R)-1-[Benzyl(methyl)amino]propan-2-ol

Procedure

Stir a mixture of 3.5 g (21.2 mmol) (2R)-1-(benzylamino)propan-2-ol [F. L. Delft, Synthesis 1997, 4, 450-454], 1.85 ml (2.0 g, 23.3 mmol) of a 35% aqueous formaldehyde solution and 3.6 ml (4.4 g, 95.3 mmol) formic acid for 16 h under reflux. After cooling to room temperature, first neutralize with 45% sodium hydroxide solution and then adjust to a pH value of 9. Extract with ethyl acetate. Wash the organic phase three times with 10 ml water each time, dry over sodium sulphate and filter. Concentrate the filtrate by vacuum evaporation, and dry. 3.08 g (78% of theor.) of the desired product is obtained.

Workup

  1. temperatureunder reflux
  2. extractionExtract with ethyl acetate
  3. washWash the organic phase three times with 10 ml water each time
  4. dry with materialdry over sodium sulphate
  5. filtrationfilter
  6. concentrationConcentrate the filtrate
  7. customby vacuum evaporation
  8. customdry

Sources & evidence

ORD record
ord-a2308d5dd8454240b62011e2e68335f4
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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