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

HRID 13013Notes

Reaction equation

HRID 13013 reaction equation
C(OC(=O)[NH:7][C@@H:8]([CH3:19])[C@@H:9]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH3:18])=[CH:13][CH:12]=1)[OH:10])(C)(C)C.Cl>C(#N)C.O>[NH2:7][C@@H:8]([CH3:19])[C@@H:9]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH3:18])=[CH:13][CH:12]=1)[OH:10]

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-a70a7dce29da43beb5ea17ee1544b178
Source dataset
uspto-grants-2010_06
Patent number
US07728030B2

Reaction notes

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