1,8-Diazabicyclo(5.4.0)undec-7-ene → (R)-3-((S)-1-(4-bromophenyl)ethyl)-6-(2-methylallyl)-6-phenyl-1,3-oxazinan-2-one

HRID 1640749Notes

Reaction equation

HRID 1640749 reaction equation
Cl[CH2:2][CH2:3][C:4]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([OH:9])[CH2:5][C:6]([CH3:8])=[CH2:7].[Br:16][C:17]1[CH:22]=[CH:21][C:20]([C@@H:23]([N:25]=[C:26]=[O:27])[CH3:24])=[CH:19][CH:18]=1.C1CCN2C(=NCCC2)CC1>C1COCC1.CCOC(C)=O>[Br:16][C:17]1[CH:18]=[CH:19][C:20]([C@@H:23]([N:25]2[CH2:2][CH2:3][C@:4]([CH2:5][C:6]([CH3:8])=[CH2:7])([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[O:9][C:26]2=[O:27])[CH3:24])=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 75688421-bromo-4-[(1S)-1-isocyanatoethyl]benzeneHCID 595323881-Chlor-5-methyl-3-phenylhex-5-en-3-ol

Product 1

HCID 46830455(R)-3-((S)-1-(4-bromophenyl)ethyl)-6-(2-methylallyl)-6-phenyl-1,3-oxazinan-2-oneYield 30.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-chloro-5-methyl-3-phenylhex-5-en-3-ol (2.9 g, 13 mmol), (S)-1-bromo-4-(1-isocyanatoethyl)benzene (3.5 g, 16 mmol), and DBU (8 g, 33 mmol) in THF (80 mL) was heated at reflux overnight. The mixture was diluted with EtOAc, and washed with 1N aq HCl. The aqueous phase was extracted with EtOAc (3×), and the combined organic phase was dried over Na2SO4. After the solvents were evaporated, the crude product was purified by column chromatography to give (R)-3-((S)-1-(4-bromophenyl)-ethyl)-6-(2-methylallyl)-6-phenyl-1,3-oxazinan-2-one (1.62 g, yield: 30%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. washwashed with 1N aq HCl
  4. extractionThe aqueous phase was extracted with EtOAc (3×)
  5. dry with materialthe combined organic phase was dried over Na2SO4
  6. customAfter the solvents were evaporated
  7. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-03015bea4bd34e0da67f9519e9bf3474
Source dataset
uspto-grants-2012_02
Patent number
US08114868B2

Reaction notes

Loading…