2-Propanol, 1-amino-2-methyl- → 2-Methyl-1-(tetrahydro-pyran-4-ylamino)-propan-2-ol

HRID 2273073Notes

Reaction equation

HRID 2273073 reaction equation
[NH2:1][CH2:2][C:3]([CH3:6])([OH:5])[CH3:4].[O:7]1[CH2:12][CH2:11][C:10](=O)[CH2:9][CH2:8]1.C([BH3-])#N.[Na+].C([O-])(O)=O.[Na+]>CO.C(O)(=O)C>[CH3:4][C:3]([OH:5])([CH3:6])[CH2:2][NH:1][CH:10]1[CH2:11][CH2:12][O:7][CH2:8][CH2:9]1

Participants

7

Reactant 4

HCID 951022-Propanol, 1-amino-2-methyl-HCID 121599Tetrahydro-4H-pyran-4-oneHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 535349472-Methyl-1-(tetrahydro-pyran-4-ylamino)-propan-2-ol

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×

Procedure

2.75 g of 1-amino-2-methylpropan-2-ol are dissolved in 20 ml of MeOH. 1.71 ml of glacial acetic acid are added dropwise under an inert atmosphere. 2 g of tetrahydropyran-4-one in 10 ml of MeOH are added, the mixture is stirred for 30 minutes at room temperature and 1.98 g of sodium cyanoborohydride are added. The resulting mixture is stirred under an inert atmosphere for 15 hours. The reaction medium is poured into saturated aqueous NaHCO3 solution (100 ml). The resulting mixture is stirred for 30 minutes and then extracted with 4 times 100 ml of DCM. The organic phase is dried over Na2SO4, filtered and evaporated without heating. The MeOH contained in the aqueous phase is evaporated off and the extraction, drying, filtration and evaporation operation is repeated 3 times. 2.8 g of 2-methyl-1-((tetrahydro-2H-pyran-4-yl)amino)propan-2-ol are recovered in total.

Workup

  1. stirringThe resulting mixture is stirred under an inert atmosphere for 15 hours
  2. stirringThe resulting mixture is stirred for 30 minutes
  3. extractionextracted with 4 times 100 ml of DCM
  4. dry with materialThe organic phase is dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. temperaturewithout heating
  8. customis evaporated off
  9. extractionthe extraction
  10. customdrying
  11. filtrationfiltration and evaporation operation
  12. custom2.8 g of 2-methyl-1-((tetrahydro-2H-pyran-4-yl)amino)propan-2-ol are recovered in total

Sources & evidence

ORD record
ord-a9a91d309bf9476cb62b726e425cdcd1
Source dataset
uspto-grants-2015_09
Patent number
US09120812B2

Reaction notes

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