N-methyl-2-pyrrolidone → (S)-3-((S)-1-(4-bromophenyl)ethyl)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one

HRID 1406609Notes

Reaction equation

HRID 1406609 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]([CH2:20][CH2:21][C@@:22]([OH:34])([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:23][C:24]([OH:27])([CH3:26])[CH3:25])[C:11](=O)[O:12]C2C=CC=CC=2)[CH3:9])=[CH:4][CH:3]=1.CN1C(=O)CCC1.[OH-].[K+]>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:20][CH2:21][C@:22]([CH2:23][C:24]([OH:27])([CH3:26])[CH3:25])([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[O:34][C:11]2=[O:12])[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 14797Potassium HydroxideHCID 68024116HCID 68024116, compound

Product 1

HCID 44599033(S)-3-((S)-1-(4-bromophenyl)ethyl)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A flask is charged with phenyl (S)-1-(4-bromophenyl)ethyl((S)-3,5-dihydroxy-5-methyl-3-phenylhexyl)carbamate (25.0 g, 47.5 mmol) and NMP (125 mL). The resultant solution is treated with 50 wt. % aqueous KOH (12.5 mL), stirred at 25° C. for 1 hour, and treated with water (250 mL). The resultant slurry is stirred at 25° C. for 1 hour, and the solids collected by filtration. The solids are then washed with water and heptane, and dried under vacuum at 50° C. for 18 hours to provide 6 as a white solid. Yield: 19.7 g, 95.1%; 99.1%. purity by weight.

Workup

  1. stirringThe resultant slurry is stirred at 25° C. for 1 hour
  2. filtrationthe solids collected by filtration
  3. washThe solids are then washed with water and heptane
  4. customdried under vacuum at 50° C. for 18 hours

Sources & evidence

ORD record
ord-9aedcc0f85604d3aba99788b0018faf8
Source dataset
uspto-grants-2014_12
Patent number
US08916701B2

Reaction notes

Loading…