1,8-Diazabicyclo(5.4.0)undec-7-ene → 6-(4-Fluorophenyl)-6-(2-methylallyl)-1,3-oxazinan-2-one

HRID 1640724Notes

Reaction equation

HRID 1640724 reaction equation
Cl[CH2:2][CH2:3][C:4]([C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)([OH:9])[CH2:5][C:6]([CH3:8])=[CH2:7].BrC1C=CC=CC=1[C@@H]([N:26]=[C:27]=[O:28])C.C1CCN2C(=NCCC2)CC1>C1COCC1.CCOC(C)=O>[F:16][C:13]1[CH:14]=[CH:15][C:10]([C:4]2([CH2:5][C:6]([CH3:8])=[CH2:7])[O:9][C:27](=[O:28])[NH:26][CH2:2][CH2:3]2)=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 596356741-Chloro-3-(4-fluorophenyl)-5-methylhex-5-en-3-olHCID 86649409(S)-(-)-1-(-bromophenyl)ethyl isocyanate

Product 1

HCID 866494086-(4-Fluorophenyl)-6-(2-methylallyl)-1,3-oxazinan-2-oneYield 65.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-chloro-3-(4-fluorophenyl)-5-methylhex-5-en-3-ol (3.15 g, 13 mmol), (S)-(−)-1-(-bromophenyl)ethyl isocyanate (3.5 g, 16 mmol), and DBU (8 g, 33 mmol) in THF (80 mL) was heated to reflux for 25 h. The mixture was diluted with EtOAc and washed with 1 N aq HCl. The aqueous phase was extracted with EtOAc (3 x). The combined organic phase was dried over Na2SO4. After the solvents were evaporated, the crude product was purified by column to give (R)-3-(S)-1-(4-bromophenyl)-ethyl)-6-(4-fluorophenyl)-6-(2-methylallyl)-1,3-oxazinan-2-one (2.13 g, yield: 38%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 25 h
  3. washwashed with 1 N aq HCl
  4. extractionThe aqueous phase was extracted with EtOAc (3 x)
  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

Sources & evidence

ORD record
ord-9581f43c9722405aaf02ed7f6f8f4ef0
Source dataset
uspto-grants-2012_02
Patent number
US08114868B2

Reaction notes

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