HCID 85675373, compound → HCID 436268, compound

HRID 850297Notes

Reaction equation

HRID 850297 reaction equation
CO[N:3]=[C:4]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1>C1COCC1>[NH2:3][CH:4]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1

Participants

3

Reactant 1

HCID 85675373HCID 85675373, compound

Product 1

HCID 436268HCID 436268, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of a mixture of syn- and anti- isomers of 2-(4-methoxyphenyl)-1-phenyl-1-ethanone-O-methyl oxime (10, 1.65 g, 6.46 mmol) in THF (40 ml, freshly distilled from sodium benzophenone ketyl) under nitrogen was added borane-tetrahydrofuran solution (21.2 ml, 21.2 nmmol, 1.0 M solution, Aldrich) at room temperature. The resulting pale yellow solution was refluxed overnight, and cooled in an ice water bath. Water (50 ml) was carefully added to quench, followed by 20% NaOH (50 ml). The resulting colorless bi-phasic mixture was refluxed with vigorous magnetic stirring overnight, and allowed to cool to room temperature. Hexanes (40 ml) were added, and the layers separated. The aqueous portion was extracted with hexanes (1×40 ml). The combined organic portions were dried over potassium carbonate, and concentrated in vacuo to afford a colorless, slightly cloudy syrup. This syrup was purified by column chromatography on neutral alumina (I, 15 g) using an elution gradient of chloroform to 10% methanol/chloroform. The amine 15 was isolated as 1.263 g of a clear, colorless syrup (86% yield): Rf 0.20 (5% methanol/chloroform); IR (CDCl3) 3376 (w), 3316 (w), 3068 (w), 3031 (w), 3007 (w), 2965 (m), 2940 (m), 2910 (m), 2834 (m), 1614 (m), 1584 (m), 1514 (s), 1493 (m), 1466 (m), 1454. (m), 1441 (m), 1300 (m), 1245 (s), 1179 (m), 1106 (w), 1033 (m); 1H NMR (CDCl3) δ7.40-7.24 (m, 5H), 7.11 (d, J=8.6 Hz, 2H), 6.85 (d, 3=8.6 Hz, 2H), 4.18 (dd, J=8.6, 4.9 Hz, 1H), 3.81 (s, 3H), 2.98 (dd, J=13.5, 4.9 Hz, 1H), 2.79 (dd, J=13.5, 8.7), 1.49 (s, 2H). Low resolution mass spec. 228(M+1, 26), 211(49), 121(44), 107(69), 106(100), 79(100).

Workup

  1. distillationfreshly distilled from sodium benzophenone ketyl) under nitrogen
  2. additionwas added borane-tetrahydrofuran solution (21.2 ml, 21.2 nmmol, 1.0 M solution, Aldrich) at room temperature
  3. temperatureThe resulting pale yellow solution was refluxed overnight
  4. temperaturecooled in an ice water bath
  5. additionWater (50 ml) was carefully added
  6. customto quench
  7. temperatureThe resulting colorless bi-phasic mixture was refluxed with vigorous
  8. additionHexanes (40 ml) were added
  9. customthe layers separated
  10. extractionThe aqueous portion was extracted with hexanes (1×40 ml)
  11. dry with materialThe combined organic portions were dried over potassium carbonate
  12. concentrationconcentrated in vacuo
  13. customto afford a colorless, slightly cloudy syrup
  14. customThis syrup was purified by column chromatography on neutral alumina (I, 15 g)

Sources & evidence

ORD record
ord-711ba3b7468647138dd53e52a14d45a4
Source dataset
uspto-grants-2000_01
Patent number
US06017910

Reaction notes

Loading…