Hydrochloric Acid → (1R,2S)-2-Amino-1-(4-ethylphenyl)-1-propanol

HRID 1098778Notes

Reaction equation

HRID 1098778 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([OH:20])[C@@H:10]([NH:12]C(=O)OC(C)(C)C)[CH3:11])=[CH:5][CH:4]=1)[CH3:2].Cl>C(#N)C.O>[NH2:12][C@@H:10]([CH3:11])[C@@H:9]([C:6]1[CH:7]=[CH:8][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=1)[OH:20]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59339896tert-butyl[(1S,2R)-2-(4-ethylphenyl)-2-hydroxy-1-methylethyl]carbamate

Product 1

HCID 28743543(1R,2S)-2-Amino-1-(4-ethylphenyl)-1-propanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

To a stirred solution of tert-butyl [(1S,2R)-2-(4-ethylphenyl)-2-hydroxy-1-methylethyl]carbamate (450 mg, 1.51 mmol) in acetonitrile (10 ml) was added aq. HCl (6 N, 3 ml), and stirring was continued for 3.5 h. Then the mixture was diluted with water (10 ml), and acetonitrile was removed in vacuo. The mixture was washed with dichloromethane (20 ml). The aqueous layer was then made alkaline (pH≈10) by addition of aq. NaOH (10 N), and extracted with dichloromethane (3×20 ml). The combined organic extracts were dried with Na2SO4, the solvent was removed in vacuo to afford white solid, 280 mg (97%).

Workup

  1. customwas removed in vacuo
  2. washThe mixture was washed with dichloromethane (20 ml)
  3. additionby addition of aq. NaOH (10 N)
  4. extractionextracted with dichloromethane (3×20 ml)
  5. dry with materialThe combined organic extracts were dried with Na2SO4
  6. customthe solvent was removed in vacuo
  7. customto afford white solid, 280 mg (97%)

Sources & evidence

ORD record
ord-1f448a58e32f48c1b89c8cf1c6703a8c
Source dataset
uspto-grants-2012_03
Patent number
US08143290B2

Reaction notes

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