Sodium Hydroxide → 1-[4-(2-Tert-butyl-5-nitro-phenyl)-but-3-enyl]-pyrrolidine

HRID 2109598Notes

Reaction equation

HRID 2109598 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[CH:14]=[CH:15][CH2:16][CH:17]=O)([CH3:4])([CH3:3])[CH3:2].[NH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+].[OH-].[Na+]>C1COCC1.CCOCC.CC(O)=O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[CH:14]=[CH:15][CH2:16][CH2:17][N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)([CH3:4])([CH3:3])[CH3:2]

Participants

9

Reactant 5

HCID 14798Sodium HydroxideHCID 31268PyrrolidineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 738566804-(2-tert-Butyl-5-nitro-phenyl)-but-3-enal

Product 1

HCID 666886581-[4-(2-Tert-butyl-5-nitro-phenyl)-but-3-enyl]-pyrrolidine

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-(2-tert-Butyl-5-nitro-phenyl)-but-3-enal (895 mg) was dissolved in 40 ml THF, and to the solution was added pyrrolidine (0.317 ml). To the deep orange solution was added NaBH(OAc)3 (1.151 g) and glacial AcOH (0.207 ml). The reaction was stirred at RT overnight, then treated with saturated aqueous NaHCO3 and diluted with Et2O and some 1N NaOH. The layers were separated, and the organic layer was extracted with aqueous 2 N HCl. The acidic aqueous layer was basified to pH>12 with 6 N NaOH, extracted with Et2O, brine-washed, dried over Na2SO4, filtered, and concentrated in vacuo to provide 1-[4-(2-tert-butyl-5-nitro-phenyl)-but-3-enyl]-pyrrolidine as a orange-brown oil.

Workup

  1. customThe layers were separated
  2. extractionthe organic layer was extracted with aqueous 2 N HCl
  3. extractionextracted with Et2O, brine-
  4. washwashed
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-db45577f12784d0eb2ed7a6f32253e3f
Source dataset
uspto-grants-2009_04
Patent number
US07514564B2

Reaction notes

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