Hydrochloric Acid → (E)-(2S)-2-Amino-5-phenyl-hex-4-en-1-ol

HRID 885164Notes

Reaction equation

HRID 885164 reaction equation
C(OC([N:8]1[C@@H:12]([CH2:13]/[CH:14]=[C:15](/[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)\[CH3:16])[CH2:11][O:10]C1(C)C)=O)(C)(C)C.Cl>O1CCOCC1.C(OCC)(=O)C>[NH2:8][C@@H:12]([CH2:13]/[CH:14]=[C:15](/[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)\[CH3:16])[CH2:11][OH:10]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67177964(4S)-2,2-Dimethyl-4-((E)-3-phenyl-but-2-enyl)-oxazolidine-3-carboxylic acid tert-butyl ester

Product 1

HCID 67177671(E)-(2S)-2-Amino-5-phenyl-hex-4-en-1-ol

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred solution of (4S)-2,2-dimethyl-4-((E)-3-phenyl-but-2-enyl)-oxazolidine-3-carboxylic acid tert-butyl ester (1.15 g) in dioxane (10 ml) at room temperature was added a 4 M solution of hydrogen chloride in dioxane (17.4 ml solution) and stirring was continued at room temperature overnight. The mixture was taken up in ethyl acetate and washed sequentially with aqueous sodium hydroxide solution (1 N), water and saturated brine. The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (SiO2, heptane/dichloromethane gradient; eluant containing 1% aq. ammonia) to yield a yellow oil, (185 mg, 28%); MS (ISP): 192.1 ([M+H]+).

Workup

  1. washwashed sequentially with aqueous sodium hydroxide solution (1 N), water and saturated brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography (SiO2, heptane/dichloromethane gradient; eluant containing 1% aq. ammonia)
  5. customto yield a yellow oil, (185 mg, 28%)

Sources & evidence

ORD record
ord-0a1f4012f1224708a56832c656cf2989
Source dataset
uspto-grants-2012_08
Patent number
US08242153B2

Reaction notes

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