Lithium hydroxide, monohydrate → HCID 58155345, compound

HRID 1929470Notes

Reaction equation

HRID 1929470 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:17])=[C:6]([C:8]2([CH:14]3[CH2:16][CH2:15]3)[CH2:12][O:11]C(=O)[NH:9]2)[CH:7]=1.O.[OH-].[Li+]>C(O)C.O>[NH2:9][C:8]([C:6]1[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[F:17])([CH:14]1[CH2:16][CH2:15]1)[CH2:12][OH:11]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 58155231HCID 58155231, compound

Product 1

HCID 58155345HCID 58155345, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A solution of the crude (RS)-4-(5-bromo-2-fluoro-phenyl)-4-cyclopropyl-oxazolidin-2-one (4.802 g) in ethanol (25 ml) and water (125 ml) was treated with lithium hydroxide monohydrate (6.7 g, 160 mmol) and the reaction mixture was stirred at 100° C. overnight. For the workup, the reaction mixture was extracted with dichloromethane, the combined organic layers were washed with water, then dried over sodium sulfate and evaporated. The crude product was purified by chromatography on an Isolute flash NH2 column using a gradient of heptane/ethyl acetate as the eluent. (RS)-2-amino-2-(5-bromo-2-fluoro-phenyl)-2-cyclopropyl-ethanol was obtained as a yellow oil (2.27 g, 52% of theory). Mass (calculated) C11H13BrFNO [274.132]; (found) [M+H]+=274, [M+2-H]+=276.

Workup

  1. extractionFor the workup, the reaction mixture was extracted with dichloromethane
  2. washthe combined organic layers were washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe crude product was purified by chromatography on an Isolute flash NH2 column

Sources & evidence

ORD record
ord-9becbff5e2714d12860e427a55575f28
Source dataset
uspto-grants-2012_05
Patent number
US08188079B2

Reaction notes

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