Hydrochloric Acid → HCID 57667107, compound

HRID 600833Notes

Reaction equation

HRID 600833 reaction equation
C(OC([N:8]1[C@H:12]([CH2:13][N:14]([CH2:21][CH3:22])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:11][O:10]C1(C)C)=O)(C)(C)C.Cl>O1CCOCC1>[NH2:8][C@H:12]([CH2:13][N:14]([CH2:21][CH3:22])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:11][OH:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57667084HCID 57667084, compound

Product 1

HCID 57667107HCID 57667107, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of (R)-4-[(ethyl-phenyl-amino)-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (608 mg) at r.t. in dioxane (5.5 ml) under an argon atmosphere was added HCl solution (4 M in dioxane; 4.54 ml). The mixture was stirred at r.t. overnight and concentrated. The residue was taken up in EtOAc and washed with 1N NaOH. The aqueous layer was back extracted with EtOAc. The combined organics were washed with brine, dried over MgSO4 and concentrated. The crude product was purified by column chromatography (Isolute® SPE flash NH2 column, aminopropyl-functionalized silica; CH2Cl2/MeOH 9:1) to give (R)-2-amino-3-(ethyl-phenyl-amino)-propan-1-ol (297 mg, 84%) as off-white amorphous solid. MS (ISP): 195.3 ([M+H]+)

Workup

  1. concentrationconcentrated
  2. washwashed with 1N NaOH
  3. extractionThe aqueous layer was back extracted with EtOAc
  4. washThe combined organics were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography (Isolute® SPE flash NH2 column, aminopropyl-functionalized silica; CH2Cl2/MeOH 9:1)

Sources & evidence

ORD record
ord-d76659d9846f48f0b5f0530d241be3e1
Source dataset
uspto-grants-2011_03
Patent number
US07902238B2

Reaction notes

Loading…