Cyanamidnatrium → HCID 67053798, compound

HRID 2171740Notes

Reaction equation

HRID 2171740 reaction equation
[N:1]#[C:2][NH2:3].[Na].[CH3:5][C:6]1([CH3:21])[CH2:15][CH2:14][CH2:13][C:12]2[CH:11]=[C:10]([O:16][CH2:17][C@@H:18]3[CH2:20][O:19]3)[CH:9]=[CH:8][C:7]1=2>CO>[CH3:21][C:6]1([CH3:5])[CH2:15][CH2:14][CH2:13][C:12]2[CH:11]=[C:10]([O:16][CH2:17][CH:18]3[O:19][C:2]([NH2:3])=[N:1][CH2:20]3)[CH:9]=[CH:8][C:7]1=2

Participants

4

Reactant 2

HCID 57375518CyanamidnatriumHCID 86668127HCID 86668127, compound

Product 1

HCID 67053798HCID 67053798, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a vigorously stirred solution of sodium hydrogen cyanamide (0.52 g, 7.9 mmol) in methanol (20 mL) was added slowly (S)-2-(5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yloxymethyl)-oxirane (1.8 g, 7.9 mmol). The reaction mixture was stirred at room temperature overnight after which it was concentrated. Anhydrous diethyl ether (100 mL) was added. The resulting white precipitate was filtered and the filtrate concentrated. The residue was purified by flash chromatography (silica, 7N NH3 in methanol/methylene chloride) to give 1.0 g (46%) of 5-(5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yloxymethyl)-4,5-dihydro-oxazol-2-ylamine.

Workup

  1. concentrationwas concentrated
  2. additionAnhydrous diethyl ether (100 mL) was added
  3. filtrationThe resulting white precipitate was filtered
  4. concentrationthe filtrate concentrated
  5. customThe residue was purified by flash chromatography (silica, 7N NH3 in methanol/methylene chloride)

Sources & evidence

ORD record
ord-a0d88e70028342d09f473e50a9e0c2cd
Source dataset
uspto-grants-2015_06
Patent number
US09051331B2

Reaction notes

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