((4-Cyclohexylphenoxy)methyl)oxirane → (S)-5-(4-cyclohexyl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine

HRID 221949Notes

Reaction equation

HRID 221949 reaction equation
[N:1]#[C:2][NH2:3].[Na].[CH:5]1([C:11]2[CH:21]=[CH:20][C:14]([O:15][CH2:16][CH:17]3[CH2:19][O:18]3)=[CH:13][CH:12]=2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1>CO>[CH:5]1([C:11]2[CH:12]=[CH:13][C:14]([O:15][CH2:16][C@H:17]3[O:18][C:2]([NH2:3])=[N:1][CH2:19]3)=[CH:20][CH:21]=2)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 5743581((4-Cyclohexylphenoxy)methyl)oxiraneHCID 57375518Cyanamidnatrium

Product 1

HCID 66875140(S)-5-(4-cyclohexyl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a vigorously stirred solution of sodium hydrogen cyanamide (0.64 g, 10 mmol) in methanol (10 mL) was added dropwise 2-(4-cyclohexyl-phenoxymethyl)-oxirane (2.32 g, 10 mmol) after which the reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated to remove methanol. Anhydrous diethyl ether (50 mL) was added after which the resulting white precipitate was removed by filtration through celite and the filtrate concentrated. The residue was purified by flash chromatography (silica, 7N NH3 in methanol/methylene chloride) to give the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto remove methanol
  3. additionAnhydrous diethyl ether (50 mL) was added after which the resulting white precipitate
  4. customwas removed by filtration through celite
  5. concentrationthe filtrate concentrated
  6. customThe residue was purified by flash chromatography (silica, 7N NH3 in methanol/methylene chloride)

Sources & evidence

ORD record
ord-b37da95c7c1241b38dfd600d54751b3c
Source dataset
uspto-grants-2012_06
Patent number
US08207181B2

Reaction notes

Loading…