Hydrochloric Acid → (R)-4-Cyclohexyl-oxazolidin-2-one

HRID 579188Notes

Reaction equation

HRID 579188 reaction equation
[NH2:1][C@H:2]([CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)[CH2:3][OH:4].Cl.CCN(C(C)C)C(C)C.Cl[C:22](Cl)([O:24]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[CH:5]1([C@@H:2]2[CH2:3][O:4][C:22](=[O:24])[NH:1]2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 13617488(2R)-2-amino-2-cyclohexylethan-1-ol

Product 1

HCID 13347633(R)-4-Cyclohexyl-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-2-Amino-2-cyclohexyl-ethanol.HCl salt (1.0 g, 5.57 mmol, 1.0 equiv) in CH2Cl2 (30.0 mL) at 0° C. was added DIPEA (1.94 mL, 11.1 mmol, 2.0 equiv) followed by triphosgene (4.95 g, 16.7 mmol, 3.0 equiv) and the resulting solution was stirred at room temperature for 12 hours. The solution was then concentrated and the residue was diluted with EtOAc. The solution was washed with water, brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel column chromatography, (EtOAc 100%) to give product 520 mg.

Workup

  1. concentrationThe solution was then concentrated
  2. additionthe residue was diluted with EtOAc
  3. washThe solution was washed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography, (EtOAc 100%)

Sources & evidence

ORD record
ord-843538dc912c4361ab50ed643abc0dd7
Source dataset
uspto-grants-2015_05
Patent number
US09040690B2

Reaction notes

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