Sodium hydride → HCID 58109194, compound

HRID 2037524Notes

Reaction equation

HRID 2037524 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]([N:12]([CH2:17][CH2:18][C:19]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[F:30])(O)[CH2:20][CH:21]=[CH2:22])[C:13](=[O:16])[O:14]C)[CH3:11])=[CH:6][CH:5]=1>C1COCC1>[CH2:20]([C@@:19]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[F:30])[O:14][C:13](=[O:16])[N:12]([C@H:10]([C:7]2[CH:8]=[CH:9][C:4]([Br:3])=[CH:5][CH:6]=2)[CH3:11])[CH2:17][CH2:18]1)[CH:21]=[CH2:22].[CH2:20]([C@:19]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[F:30])[O:14][C:13](=[O:16])[N:12]([C@H:10]([C:7]2[CH:8]=[CH:9][C:4]([Br:3])=[CH:5][CH:6]=2)[CH3:11])[CH2:17][CH2:18]1)[CH:21]=[CH2:22]

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 58109691HCID 58109691, compound

Product 2

HCID 58109194HCID 58109194, compoundYield 35%HCID 66857816HCID 66857816, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of NaH (55 g, 1.4 mmol) in THF (10 mL) at 0° C. was added a solution of methyl (S)-1-(4-bromophenyl)ethyl(3-(2-fluorophenyl)-3-hydroxyhex-5-enyl)carbamate (300 mg, 0.68 mmol) in THF (10 mL). The resulting mixture was stirred for 10 minutes, and then was refluxed for 1 h. The reaction was quenched with saturated aq NH4Cl solution, and the solution was extract with EtOAc. The combine organic layer washed with brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by preparative TLC to afford (R)-6-allyl-3-((S)-1-(4-bromophenyl)ethyl)-6-(2-fluorophenyl)-1,3-oxazinan-2-one (100 mg, 35%) and (S)-6-allyl-3-((S)-1-(4-bromophenyl)ethyl)-6-(2-fluorophenyl)-1,3-oxazinan-2-one (100 mg, 35%).

Workup

  1. temperaturewas refluxed for 1 h
  2. customThe reaction was quenched with saturated aq NH4Cl solution
  3. extractionthe solution was extract with EtOAc
  4. washThe combine organic layer washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-3da3b41e2d674dcda62cd6f0c5ad8f86
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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