HCID 58109706, compound → HCID 25182140, compound

HRID 2037410Notes

Reaction equation

HRID 2037410 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:8]([CH2:13][CH2:14][C:15](=[O:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9](=[O:12])OC)[CH:5]=[CH:6][CH:7]=1.[CH2:23]([Mg]Br)[CH:24]=[CH2:25]>C1COCC1>[CH2:25]([C:15]1([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[O:22][C:9](=[O:12])[N:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=2)[CH2:13][CH2:14]1)[CH:24]=[CH2:23]

Participants

4

Reactant 2

HCID 58109706HCID 58109706, compoundHCID 178455850HCID 178455850, compound

Product 1

HCID 25182140HCID 25182140, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-bromophenyl(3-oxo-3-phenylpropyl)carbamate (250 mg, 0.69 mmol) in dry THF (2 mL) was added dropwise 1 M allylmagnesium bromide (10 mL) −78° C. The reaction mixture was stirred at rt for 3 h. The resulting mixture was quenched with sattd aq NH4Cl and extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated to give 6-allyl-3-(3-bromophenyl)-6-phenyl-1,3-oxazinan-2-one (120 mg, 47%). 1H NMR (400 MHz, CDCl3): δ=2.48 (m, 2H), 2.55-2.7 (m, 2H), 3.23 (m, 1H), 3.51 (m, 1H), 5.04 (m, 2H), 5.72 (m, 1H), 7.01 (m, 1H), 7.11 (m, 1H), 7.23 (m, 1H), 7.3 (m, 1H), 7.35 (m, 6H).

Workup

  1. customThe resulting mixture was quenched with sattd aq NH4Cl
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4cff57780e9f411fb70045aaf9728b6b
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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