Isopropanol → tert-Butyl (1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-[(3-methoxybenzyl)amino]propylcarbamate

HRID 1350985Notes

Reaction equation

HRID 1350985 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C@H:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C@H:11]2[CH2:13][O:12]2)[CH:5]=[C:6]([F:8])[CH:7]=1.[C@@H:22]1([NH2:32])[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)CCC1.C[CH:34]([OH:36])C>>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([F:8])[CH:7]=1)[CH2:9][C@H:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C@H:11]([OH:12])[CH2:13][NH:32][CH2:22][C:31]1[CH:30]=[CH:29][CH:28]=[C:27]([O:36][CH3:34])[CH:26]=1

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 70580741-Aminotetralin, (S)-HCID 9922319tert-Butyl ((S)-2-(3,5-difluorophenyl)-1-((S)-oxiran-2-yl)ethyl)carbamate

Product 1

HCID 11441951tert-Butyl (1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-[(3-methoxybenzyl)amino]propylcarbamate

Procedure

A mixture of tert-butyl (1S)-2-(3,5-difluorophenyl)-1-[(2S)-oxiranyl]ethylcarbamate (V, 500 mg, 1.67 mmol) and 3-methoxybenzylamine (VI, 0.34g, 2.51 mmol) in 2-propanol (3 mL) is heated at reflux overnight, allowed to cool to 20–25 degrees C., and concentrated under reduced pressure. The residue is crystallized from ethyl acetate/hexanes and collected by filtration to afford tert-butyl (1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-[(3-methoxybenzyl)amino]propylcarbamate (VII, 575 mg) as a solid: ESI-MS (m/z): 437 [M+H]+.

Workup

  1. temperatureis heated
  2. temperatureat reflux overnight
  3. temperatureto cool to 20–25 degrees C
  4. concentration, and concentrated under reduced pressure
  5. customThe residue is crystallized from ethyl acetate/hexanes
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-7258bd5b8d0548298260fde6a6e3fa44
Source dataset
uspto-grants-2007_05
Patent number
US07214715B2

Reaction notes

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