Cyanamidnatrium → HCID 67053820, compound

HRID 2171737Notes

Reaction equation

HRID 2171737 reaction equation
[N:1]#[C:2][NH2:3].[Na].[CH3:5][C:6]([O:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[CH2:17][CH2:16][CH2:15]2)([C@@H:8]1[CH2:10][O:9]1)[CH3:7]>CO>[CH3:5][C:6]([O:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[CH2:17][CH2:16][CH2:15]2)([CH:8]1[O:9][C:2]([NH2:3])=[N:1][CH2:10]1)[CH3:7]

Participants

4

Reactant 2

HCID 57375518CyanamidnatriumHCID 86668126HCID 86668126, compound

Product 1

HCID 67053820HCID 67053820, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a vigorously stirred solution of sodium hydrogen cyanamide (0.21 g, 3.21 mmol) in methanol (10 mL) was added slowly (S)-2-(1,1-dimethyl-indan-5-yloxymethyl)-oxirane (0.57 g, 3.21 mmol). The reaction mixture was stirred at room temperature overnight after which the reaction mixture was concentrated. Anhydrous diethyl ether (50 mL) was added. The resulting white precipitate was filtered through Celite and the filtrate concentrated. The residue was purified by flash chromatography (silica, 7N NH3 in methanol/methylene chloride) to give 0.41 g (49%) of 5-(1,1-dimethyl-indan-5-yloxymethyl)-4,5-dihydro-oxazol-2-ylamine.

Workup

  1. concentrationwas concentrated
  2. additionAnhydrous diethyl ether (50 mL) was added
  3. filtrationThe resulting white precipitate was filtered through Celite
  4. concentrationthe filtrate concentrated
  5. customThe residue was purified by flash chromatography (silica, 7N NH3 in methanol/methylene chloride)

Sources & evidence

ORD record
ord-6925a7995f484976921716c35a678614
Source dataset
uspto-grants-2015_06
Patent number
US09051331B2

Reaction notes

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