Methanol → (S)-2-(6-Methoxynaphthalen-2-yl)propyl carbamate

HRID 2389039

Reaction equation

HRID 2389039 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C@H:13]([CH3:16])[CH2:14][OH:15])[CH:7]=[CH:6]2.ClC(Cl)(Cl)[C:19]([N:21]=C=O)=[O:20].CO.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C@H:13]([CH3:16])[CH2:14][O:15][C:19](=[O:20])[NH2:21])[CH:7]=[CH:6]2

Participants

7

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 76400Trichloroacetyl isocyanateHCID 3032818Naproxol

Product 1

HCID 67413984(S)-2-(6-Methoxynaphthalen-2-yl)propyl carbamateYield 57.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To (S)-2-(6-methoxy-naphthalen-2-yl)-propan-ol (8.0 g, 37 mmol) in CH2Cl2 (200 mL) at 0° C. under N2 was added trichloroacetyl isocyanate (5.5 mL, 44 mmol). After the mixture was stirred at room temperature for 1 hr, the solvent was concentrated. The residue was treated MeOH (300 mL), water (40 mL) and potassium carbonate (21 g, 0.15 mol) and stirred at RT for 2 hrs to form white precipitate. The precipitate was collected by filtration and dissolved with CH2Cl2. The organic phase was washed with water, dried over MgSO4 and concentrated to give 5.5 g of white precipitate (57%).

Workup

  1. concentrationthe solvent was concentrated
  2. stirringstirred at RT for 2 hrs
  3. customto form white precipitate
  4. filtrationThe precipitate was collected by filtration
  5. dissolutiondissolved with CH2Cl2
  6. washThe organic phase was washed with water
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-9efa516740a84480af5b5399c4c9b9c7
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Linked notes

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