Pyridine → (1S,6R,9aR)-6-(4-chlorophenyl)-1-methyltetrahydro-[1,4]oxazino[3,4-c][1,4]oxazine-3,4-dione

HRID 1677067Notes

Reaction equation

HRID 1677067 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].ClCCl.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C@H:17]2[NH:22][C@@H:21]([C@@H:23]([OH:25])[CH3:24])[CH2:20][O:19][CH2:18]2)=[CH:13][CH:12]=1.N1C=CC=CC=1>O>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([C@@H:17]2[CH2:18][O:19][CH2:20][C@@H:21]3[C@H:23]([CH3:24])[O:25][C:1](=[O:5])[C:2](=[O:3])[N:22]23)=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 68716014(S)-1-[(3R,5R)-5-(4-chlorophenyl)morpholine-3-yl]ethanol

Product 1

HCID 67374837(1S,6R,9aR)-6-(4-chlorophenyl)-1-methyltetrahydro-[1,4]oxazino[3,4-c][1,4]oxazine-3,4-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under ice-cooling, oxalyl chloride (833 μL) was added dropwise into a dichloromethane (15 mL) solution of (S)-1-[(3R,5R)-5-(4-chlorophenyl)morpholin-3 yl]ethanol (833 mg) and pyridine (4 mL). Stirring was continued for 30 minutes at the same temperature and for 1 hour at room temperature. Water was added to the reaction solution, and the organic layer was partitioned. The resultant was dried over anhydrous magnesium sulfate, and the solvent was removed under a vacuum. The residue was purified by silica gel column chromatography (heptane/ethyl acetate→ethyl acetate), and the title compound (686 mg) was obtained. The physical property values are as follows.

Workup

  1. temperatureUnder ice-cooling
  2. customthe organic layer was partitioned
  3. dry with materialThe resultant was dried over anhydrous magnesium sulfate
  4. customthe solvent was removed under a vacuum
  5. customThe residue was purified by silica gel column chromatography (heptane/ethyl acetate→ethyl acetate)

Sources & evidence

ORD record
ord-dbc244e570754fc5af2c93c7eec86974
Source dataset
uspto-grants-2011_08
Patent number
US08008293B2

Reaction notes

Loading…