Cyclohexylamine → HCID 69359883, compound

HRID 852663Notes

Reaction equation

HRID 852663 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][C@H:8]([C@H:16]1[CH2:18][O:17]1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[CH:20]1([NH2:26])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>CCO>[C:1]([O:5][C:6](=[O:19])[NH:7][C@@H:8]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C@H:16]([OH:17])[CH2:18][NH:26][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 9903372(2S,3S)-(-)-3-tert-Butoxycarbonylamino-1,2-epoxy-4-phenylbutane

Product 1

HCID 69359883HCID 69359883, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

((S)-(S)-1-Oxiranyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester (D101) (10 g, 38 mmol, 1 equiv) [Chirex 1819W94 Lot#9924382] was dissolved in EtOH (100 ml) and cyclohexylamine (13 ml, 114 mmol, 3 equiv) was added. The resulting mixture was heated, under an atmosphere of nitrogen, for 12 h at reflux temperature. The mixture was cooled and the solvent was removed by evaporation in vacuo. The resulting white solid was washed with H2O and then with Et2O before drying in vacuo to give ((1S,2R)-1-benzyl-3-cyclohexylamino-2-hydroxy-propyl)-carbamic acid tert-butyl ester (H1) (9.0 g, 66%). [M+H]+=363.2

Workup

  1. temperatureThe resulting mixture was heated, under an atmosphere of nitrogen, for 12 h
  2. temperatureat reflux temperature
  3. temperatureThe mixture was cooled
  4. customthe solvent was removed by evaporation in vacuo
  5. washThe resulting white solid was washed with H2O
  6. dry with materialwith Et2O before drying in vacuo

Sources & evidence

ORD record
ord-d5f5a12673b544a7bbeb3ce1f426948a
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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