1,8-Diazabicyclo(5.4.0)undec-7-ene → 6-allyl-3-((S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one

HRID 2091508Notes

Reaction equation

HRID 2091508 reaction equation
Cl[CH2:2][CH2:3][C:4]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)([OH:8])[CH2:5][CH:6]=[CH2:7].[N:16]([C@@H:19]([CH3:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[C:17]=[O:18].C1CCN2C(=NCCC2)CC1>C1COCC1.CCOC(C)=O>[CH2:5]([C:4]1([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[O:8][C:17](=[O:18])[N:16]([C@H:19]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH3:24])[CH2:2][CH2:3]1)[CH:6]=[CH2:7]

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 12169316(S)-3-isocyanato-2,2-dimethyl-butaneHCID 534729381-Chloro-3-(4-fluorophenyl)hex-5-en-3-ol

Product 1

HCID 584852576-allyl-3-((S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-1,3-oxazinan-2-oneYield 11.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-chloro-3-(4-fluorophenyl)hex-5-en-3-ol (500 mg, 2.19 mmol), (S)-3-isocyanato-2,2-dimethyl-butane (845 mg, 5.58 mmol), and DBU (681 mg, 5.9 mmol) in THF (10 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×). The combined organic phase was dried over Na2SO4. After the solvents were evaporated, the crude product was purified by column to give 6-allyl-3-((2S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one (80 mg, crude).

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×)
  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-bedd2c881ac34335bb6d8bf654767b92
Source dataset
uspto-grants-2013_05
Patent number
US08440658B2

Reaction notes

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