Sodium Methoxide → HCID 69059052, compound

HRID 1784346Notes

Reaction equation

HRID 1784346 reaction equation
F[C:2]1[CH:16]=[CH:15][C:5]2[C:6](=[O:14])[N:7]3[CH2:13][CH2:12][CH2:11][C@H:8]3[CH2:9][O:10][C:4]=2[CH:3]=1.[CH3:17][O-:18].[Na+]>CN(C)C=O.O>[CH3:17][O:18][C:2]1[CH:16]=[CH:15][C:5]2[C:6](=[O:14])[N:7]3[CH2:13][CH2:12][CH2:11][C@H:8]3[CH2:9][O:10][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 69058312HCID 69058312, compound

Product 1

HCID 69059052HCID 69059052, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A solution of (S)-8-fluoro-2,3,11,11a-tetrahydro-1H,5H-pyrrolo[2,1-c][1,4]-benzoxazepine-5-one (0.5 g; 2.14 mmol), prepared as described in Example 5A, and sodium methoxide (0.244 g; 4.52 mmol) in dimethylformamide (2 mL) was heated at 110° C. for 3 h. The reaction was diluted with water and extracted with ethyl acetate and the organic layer washed with water then dried (Na2SO4) and evaporated in vacuo. The crude product was purified by chromatography on silica (eluting with 5% methanol in dichloromethane) to give the title product, m.p. 104-106° C.; EIMS: m/z=234 [M+H]+

Workup

  1. extractionextracted with ethyl acetate
  2. washthe organic layer washed with water
  3. dry with materialthen dried (Na2SO4)
  4. customevaporated in vacuo
  5. customThe crude product was purified by chromatography on silica (eluting with 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-d66209a5de7c4b3787d8e73fb433a254
Source dataset
uspto-grants-2009_03
Patent number
US07504390B2

Reaction notes

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