Methylamine → (R)-3-Amino-1-phenyl-propan-1-ol

HRID 1160150Notes

Reaction equation

HRID 1160150 reaction equation
CS(O[CH2:6][CH2:7][C@H:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[OH:9])(=O)=O.C[NH2:17]>C1COCC1.CCOCC>[C:10]1([C@H:8]([OH:9])[CH2:7][CH2:6][NH2:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 14131795(R)-3-phenyl-3-(hydroxy)-propyl methanesulfonate

Product 1

HCID 11182697(R)-3-Amino-1-phenyl-propan-1-ol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (R)-3-phenyl-3-(hydroxy)-propyl methanesulfonate (3 mmol) and methylamine (10 mL, 40% in water) in THF (10 mL) is heated at 65° C. for 3 h. After cooling, the solution is diluted with ether, washed with saturated aqueous sodium bicarbonate and brine, and dried with anhydrous potassium carbonate. Concentration of extract provides (R)-3-phenyl-3-(hydroxy)-propyl amine.

Workup

  1. temperatureAfter cooling
  2. washwashed with saturated aqueous sodium bicarbonate and brine
  3. dry with materialdried with anhydrous potassium carbonate
  4. extractionConcentration of extract

Sources & evidence

ORD record
ord-2fc70354422f4514ad1198fc9b842da5
Source dataset
uspto-grants-2010_10
Patent number
US07816345B2

Reaction notes

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