Acetonitrile → (6S)-6-(3,5-dimethylphenyl)-1,3-oxazinan-2-one

HRID 537969Notes

Reaction equation

HRID 537969 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C@@H:9]([OH:15])[CH2:10][CH2:11]C(N)=O)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[C:16]([OH:19])(=O)C.C(O)(=O)C.IC1C=CC=CC=1.C(#[N:33])C>>[CH3:8][C:6]1[CH:5]=[C:4]([C@H:9]2[O:15][C:16](=[O:19])[NH:33][CH2:11][CH2:10]2)[CH:3]=[C:2]([CH3:1])[CH:7]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 12217721Iodo benzene diacetateHCID 68997524(4S)-4-(3,5-dimethylphenyl)-4-hydroxybutanamide

Product 1

HCID 57544374(6S)-6-(3,5-dimethylphenyl)-1,3-oxazinan-2-one

Procedure

A stirred solution of (4S)-4-(3,5-dimethylphenyl)-4-hydroxybutanamide (Step B; 204 mg; 0.99 mmol) and iodobenzene diacetate (317 mg; 0.99 mmol) in acetonitrile (8 mL) was heated at 40° C. for 16 h. The reaction was concentrated in vacuo and the residue purified by flash silica gel chromatography (0-100% EtOAc/hexanes gradient) to afford (6S)-6-(3,5-dimethylphenyl)-1,3-oxazinan-2-one as a white solid. LCMS=206.3 (M+1)+. 1H NMR (CDCl3, 500 MHz): δ 7.01 (s, 2H), 7.00 (s, 1H), 5.73 (s, 1H), 5.30 (dd, J=9.8, 2.8 Hz, 1H), 3.50 (dt, J=11, 4.8 Hz, 1H), 3.43-3.38 (m, 1H), 2.35 (s, 6H), 2.26-2.21 (m, 1H), 2.14-2.06 (m, 1H).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe residue purified by flash silica gel chromatography (0-100% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-046e202e277b454b86ae199ae21fa284
Source dataset
uspto-grants-2014_10
Patent number
US08865707B2

Reaction notes

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