4-tert-Butylphenyl glycidyl ether, (+)- → (S)-5-(4-tert-butyl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine

HRID 237730Notes

Reaction equation

HRID 237730 reaction equation
[N:1]#[C:2][NH2:3].[Na].[C:5]([C:9]1[CH:19]=[CH:18][C:12]([O:13][CH2:14][C@@H:15]2[CH2:17][O:16]2)=[CH:11][CH:10]=1)([CH3:8])([CH3:7])[CH3:6]>CO>[C:5]([C:9]1[CH:19]=[CH:18][C:12]([O:13][CH2:14][C@H:15]2[O:16][C:2]([NH2:3])=[N:1][CH2:17]2)=[CH:11][CH:10]=1)([CH3:6])([CH3:7])[CH3:8]

Participants

4

Reactant 2

HCID 7193734-tert-Butylphenyl glycidyl ether, (+)-HCID 57375518Cyanamidnatrium

Product 1

HCID 67060987(S)-5-(4-tert-butyl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamineYield 41%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a vigorously stirred solution of sodium hydrogen cyanamide (2.92 g, 44.5 mmol) in methanol (40 mL) was added dropwise (S)-2-(4-tert-butylphenoxymethyl)-oxirane (9.18 g, 44.5 mmol). The reaction mixture was stirred at room temperature overnight after which the reaction mixture was concentrated to remove methanol. Anhydrous diethyl ether (150 mL) was added. The resulting white precipitate was filtered through celite and the filtrate was concentrated. The residue was purified by flash chromatography (silica, 7N NH3 in methanol/methylene chloride) to give 4.53 g (41%) of (S)-5-(4-tert-butyl-phenoxymethyl)-(4,5-dihydro-oxazol-2-yl)amine.

Workup

  1. concentrationwas concentrated
  2. customto remove methanol
  3. additionAnhydrous diethyl ether (150 mL) was added
  4. filtrationThe resulting white precipitate was filtered through celite
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by flash chromatography (silica, 7N NH3 in methanol/methylene chloride)

Sources & evidence

ORD record
ord-626b2a8eccaf447a9d00c52e8afc40d5
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

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