Sodium hydride → (4aR,9aS)-4,4a,9,9a-Tetrahydroindeno[2,1-b][1,4]oxazin-3(2H)-onato

HRID 1367221Notes

Reaction equation

HRID 1367221 reaction equation
Cl[CH2:2][C:3]([NH:5][C@@H:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][C@@H:7]1[OH:15])=[O:4].[H-].[Na+]>C1COCC1>[O:15]1[CH2:2][C:3](=[O:4])[NH:5][C@@H:6]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[CH2:8][C@H:7]12

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 66973294HCID 66973294, compound

Product 1

HCID 59445883(4aR,9aS)-4,4a,9,9a-Tetrahydroindeno[2,1-b][1,4]oxazin-3(2H)-onato

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of 2-chloro-N-[(1R,2S)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]acetamide from Step A (780 mg, 3.46 mmol) in anhydrous THF (75 mL) at 0° C. was added NaH (498 mg of a 60% dispersion in oil, 12.4 mmol). The resulting mixture was stirred for 3 h, quenched with saturated aqueous NaHCO3 (20 mL) and then extracted with EtOAc (3×50 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound. MS: m/z=190 (M+1).

Workup

  1. customquenched with saturated aqueous NaHCO3 (20 mL)
  2. extractionextracted with EtOAc (3×50 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-73db0a1742db47318a0af22fa24e7a44
Source dataset
uspto-grants-2011_02
Patent number
US07893079B2

Reaction notes

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