Methanol → 3-(2-Nitrobenzylamino)-1-phenylpropanol

HRID 553403Notes

Reaction equation

HRID 553403 reaction equation
[OH:1][CH:2]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:3][C:4]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15])=O.O1CCCC1.O1CCCC1.B.CO>O1CCCC1>[N+:14]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[CH2:7][NH:6][CH2:4][CH2:3][CH:2]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[OH:1])([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 887MethanolHCID 674618943-hydroxy-N-(2-nitrobenzyl)-3-phenyl propionic acid amideHCID 178419153HCID 178419153, compound

Product 1

HCID 674614753-(2-Nitrobenzylamino)-1-phenylpropanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Hydroxy-N-(2-nitrobenzyl)-3-phenyl propionic acid amide (3.19 g, 10.6 mmol) was dissolved in tetrahydrofuran (50 ml) and under ice cooled condition, 1 M tetrahydrofuran-borane tetrahydrofuran solution (27.0 ml, 27.0 mmol) was added dropwise thereto. After the dropwise addition was finished, the reaction mixture was returned to room temperature and stirred for one hour, then heated to reflux for six hours and allowed to cool. Methanol (30 ml) was added thereto under ice cooled condition and heated to reflux for 30 minutes. After allowed to cool, the solvent was evaporated and 0.5 N hydrochloric acid water (30 ml) was added. After extracted with diethyl ether, the aqueous layer was adjusted to pH 8 with a saturated sodium hydrogen carbonate aqueous solution and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure to obtain 3-(2-nitrobenzylamino)-1-phenylpropanol.

Workup

  1. additionwas added dropwise
  2. additionAfter the dropwise addition
  3. customwas returned to room temperature
  4. temperatureheated
  5. temperatureto reflux for six hours
  6. temperatureto cool
  7. temperatureunder ice cooled condition and heated
  8. temperatureto reflux for 30 minutes
  9. temperatureto cool
  10. customthe solvent was evaporated
  11. addition0.5 N hydrochloric acid water (30 ml) was added
  12. extractionAfter extracted with diethyl ether
  13. extractionextracted with ethyl acetate
  14. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  15. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7cf58015a401428da346147e801bd328
Source dataset
uspto-grants-2011_11
Patent number
US08048825B2

Reaction notes

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