tert-Butanol → HCID 68615579, compound

HRID 859222Notes

Reaction equation

HRID 859222 reaction equation
[F:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[C:10]2[CH:15]=[CH:14][C:13]([N:16]3[C:20](=[O:21])[CH2:19][CH:18](C(O)=O)[CH2:17]3)=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1.ClC([O:28][CH2:29]C(C)C)=O.[N-:33]=[N+]=[N-].[Na+].[C:37]([OH:41])([CH3:40])([CH3:39])[CH3:38]>O1CCCC1.O.C1(C)C=CC=CC=1>[C:37]([O:41][C:29](=[O:28])[NH:33][CH:18]1[CH2:19][C:20](=[O:21])[N:16]([C:13]2[CH:14]=[CH:15][C:10](/[CH:9]=[CH:8]/[C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)=[CH:11][CH:12]=2)[CH2:17]1)([CH3:40])([CH3:39])[CH3:38]

Participants

8

Reactant 4

HCID 6386tert-ButanolHCID 33557Sodium AzideHCID 62365Isobutyl chloroformateHCID 21920044HCID 21920044, compound

Product 1

HCID 68615579HCID 68615579, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 150 mg (0.46 mmol) of (RS)-(E)-1-{4-[2-(3-fluoro-phenyl)-vinyl]-phenyl}-5-oxo-pyrrolidine-3-carboxylic acid in 2 ml of tetrahydrofurane is cooled to −15° C. and 63 mg (0.46 mmol) of isobutyl chloroformate are added dropwise. After 5 min, a solution of 60 mg (0.92 mmol) of sodium azide in 0.5 ml water is added. The mixture is stirred at 0° C. for 45 min, then left to warm to RT. Toluene is added and the diluted solution is washed with a saturated solution of sodium hydrogencarbonate. The organic layer is separated, dried over magnesium sulfate, and evaporated under reduced pressure. The residue is dissolved in 5 ml of toluene and the solution warmed to 80° C. After 30 min, 1.1 ml (1.2 mmol) of tert-butanol are added and heating is continued for 18 hours. For the working-up, the reaction mixture is evaporated and the crude product directly chromatographed on silica gel using a 95:5-mixture of dichloromethane and methanol as the eluent. After crystallisation from ether, 104 mg (57% of theory) of (RS)-(E)- (1-{4-[2-(3-fluoro-phenyl)-vinyl]-phenyl}-5-oxo-pyrrolidin-3-yl)-carbamic acid tert-butyl ester are obtained as a light yellow solid; MS: m/e=397 (M+H)+.

Workup

  1. waitleft
  2. temperatureto warm to RT
  3. washthe diluted solution is washed with a saturated solution of sodium hydrogencarbonate
  4. customThe organic layer is separated
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. dissolutionThe residue is dissolved in 5 ml of toluene
  8. temperaturethe solution warmed to 80° C
  9. waitAfter 30 min
  10. temperatureheating
  11. waitis continued for 18 hours
  12. customthe reaction mixture is evaporated
  13. customthe crude product directly chromatographed on silica gel using a 95
  14. customAfter crystallisation from ether, 104 mg (57% of theory) of (RS)-(E)- (1-{4-[2-(3-fluoro-phenyl)-vinyl]-phenyl}-5-oxo-pyrrolidin-3-yl)-carbamic acid tert-butyl ester
  15. customare obtained as a light yellow solid

Sources & evidence

ORD record
ord-3ea0022be5c24d0e8332031cae20a0c1
Source dataset
uspto-grants-2006_12
Patent number
US07151111B2

Reaction notes

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