Methanol → HCID 67281263, compound

HRID 515495Notes

Reaction equation

HRID 515495 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:14](=O)[N:13]([C@@H:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH3:17])[CH2:12][CH2:11][CH2:10][O:9]2)[CH:5]=[CH:6][CH:7]=1.CO.[OH-].[Na+]>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:14][N:13]([C@@H:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH3:17])[CH2:12][CH2:11][CH2:10][O:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 67282405HCID 67282405, compound

Product 1

HCID 67281263HCID 67281263, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(3-bromo-phenyl)-4-((R)-1-phenyl-ethyl) -[1,4]oxazepan-3-one (diastereomer 1) (9.39 g, 25.1 mmol) in tetrahydrofuran (75 ml) was added 1.0M-borane-tetrahydrofuran complex in tetrahydrofuran (75.0 ml, 75.0 mmol) at 0° C. The mixture was refluxed for 4 hours. The mixture was cooled to 0° C. and methanol (100 ml) and 6.0 N aqueous sodium hydroxide (100 ml) was added carefully. The mixture was refluxed for 2 hours and cooled to room temperature. The solvent was removed under reduced pressure. The residue was partitioned between water and chloroform. The organic layer was washed with brine, dried over sodium sulfate, concentrated in vacuo. The residue was purified by silica gel column chromatography (eluant; hexane/ethyl acetate=4/1) to afford diastereomerically pure 2-(3-bromophenyl)-4-((R)-1-phenyl-ethyl)-[1,4]oxazepane as colorless oil (8.92 g, 99%).

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. temperatureThe mixture was refluxed for 2 hours
  3. temperaturecooled to room temperature
  4. customThe solvent was removed under reduced pressure
  5. customThe residue was partitioned between water and chloroform
  6. washThe organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel column chromatography (eluant; hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-6fef8b85c25f4d11b1b562256c03f9c1
Source dataset
uspto-grants-2015_08
Patent number
US09108957B2

Reaction notes

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