Sodium hydride → HCID 86682284, compound

HRID 540461Notes

Reaction equation

HRID 540461 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:10]([OH:24])[C@@H:11]([NH:13][C:14](=[O:23])OCC2C=CC=CC=2)[CH3:12])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[H-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:10]2[O:24][C:14](=[O:23])[NH:13][C@H:11]2[CH3:12])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 86682285HCID 86682285, compound

Product 1

HCID 86682284HCID 86682284, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzyl ((1R,2S)-1-(3-chloro-4-methoxyphenyl)-1-hydroxypropan-2-yl)carbamate (0.24 g, 0.686 mmol) in THF (4.6 mL) was added NaH (0.036 g, 0.892 mmol) at 0° C. The reaction mixture was warmed to RT and stirred overnight. It was then quenched with 1N HCl (1.5 mL). This mixture was diluted with EtOAc and washed with sat. aqueous NaHCO3, water and brine. The organic phase was dried with Na2SO4 and concentrated. The residue was purified by silica gel chromatography, eluted with EtOAc to give (4S,5R)-5-(3-chloro-4-methoxyphenyl)-4-methyloxazolidin-2-one (intermediate K, 0.13 g). 1H NMR (500 MHz, CDCl3): δ 7.37 (s, 1H), 7.21 (d, 1H), 6.97 (d, 1H), 5.84 (b, 1H), 5.65 (d, 1H), 4.21 (m, 1H), 3.96 (s, 3H), 0.87 (d, 3H).

Workup

  1. customIt was then quenched with 1N HCl (1.5 mL)
  2. additionThis mixture was diluted with EtOAc
  3. washwashed with sat. aqueous NaHCO3, water and brine
  4. dry with materialThe organic phase was dried with Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography
  7. washeluted with EtOAc

Sources & evidence

ORD record
ord-c22fc06b2b024f3dafa11dd2f6d913ce
Source dataset
uspto-grants-2014_10
Patent number
US08871738B2

Reaction notes

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