Water → HCID 436268, compound

HRID 2293968Notes

Reaction equation

HRID 2293968 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.B.O1CCCC1.O>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

5

Reactant 3

HCID 962WaterHCID 2723981Borane;tetrahydrofuranHCID 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 mmol, 1.0M 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, J=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. temperatureThe resulting pale yellow solution was refluxed overnight
  3. temperaturecooled in an ice water bath
  4. customto quench
  5. temperatureThe resulting colorless bi-phasic mixture was refluxed with vigorous
  6. additionHexanes (40 ml) were added
  7. customthe layers separated
  8. extractionThe aqueous portion was extracted with hexanes (1×40 ml)
  9. dry with materialThe combined organic portions were dried over potassium carbonate
  10. concentrationconcentrated in vacuo
  11. customto afford a colorless, slightly cloudy syrup
  12. customThis syrup was purified by column chromatography on neutral alumina (I, 15 g)

Sources & evidence

ORD record
ord-943fb728f6c94880a38b545dd758c6d2
Source dataset
uspto-grants-1997_11
Patent number
US05688789

Reaction notes

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