Ammonium cerium (IV) nitrate → 2-(3-Methyl-1,2-oxazol-5-yl)morpholine

HRID 1750304Notes

Reaction equation

HRID 1750304 reaction equation
[N+]([O-])([O-])=O.[Ce+4].[NH4+].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.C([N:30]1[CH2:35][CH2:34][O:33][CH:32]([C:36]2[O:40][N:39]=[C:38]([CH3:41])[CH:37]=2)[CH2:31]1)C1C=CC=CC=1>C(#N)C.O>[CH3:41][C:38]1[CH:37]=[C:36]([CH:32]2[O:33][CH2:34][CH2:35][NH:30][CH2:31]2)[O:40][N:39]=1

Participants

4

Reactant 2

HCID 9869224Ammonium cerium (IV) nitrateHCID 86706974HCID 86706974, compound

Product 1

HCID 566104532-(3-Methyl-1,2-oxazol-5-yl)morpholine

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
25 °C

Procedure

Ammonium cerium(IV) nitrate (442 mg, 0.806 mmol) was added to a solution of 4-benzyl-2-(3-methyl-1,2-oxazol-5-yl)morpholine (C37) (100 mg, 0.39 mmol) in acetonitrile/water (5:1 mixture, 6 mL). The reaction mixture was stirred at 25° C. for 4 hours, then concentrated in vacuo; preparative thin-layer chromatography on silica gel (Eluent: 10:1 dichloromethane/methanol) provided the product as a yellow oil. Yield: 40 mg, 0.24 mmol, 62%. 1H NMR (400 MHz, CDCl3) δ 6.11 (s, 1H), 4.79 (dd, J=10.0, 2.4 Hz, 1H), 4.01 (ddd, J=11.8, 2.5, 2.4 Hz, 1H), 3.81-3.89 (m, 1H), 3.35 (dd, J=12.7, 2.5 Hz, 1H), 2.99-3.07 (m, 3H), 2.30 (s, 3H).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f76ce2bcdf964528b98da8d572a3c286
Source dataset
uspto-grants-2015_10
Patent number
US09156845B2

Reaction notes

Loading…