Tetrahydrofuran → Benzyl 3-(1,1-dimethylprop-2-en-1-yl)-3-hydroxypyrrolidine-1-carboxylate

HRID 504433Notes

Reaction equation

HRID 504433 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:3]1.Br[CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21].O1CCCC1>[Cl-].[NH4+].[Zn]>[CH3:21][C:20]([C:2]1([OH:1])[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:3]1)([CH3:22])[CH:19]=[CH2:18]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 700922-Butene, 1-bromo-3-methyl-HCID 5612031-N-Cbz-3-pyrrolidinone

Product 1

HCID 66662637Benzyl 3-(1,1-dimethylprop-2-en-1-yl)-3-hydroxypyrrolidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 25517Ammonium ChlorideSolvent

Procedure

To a suspension of benzyl 3-oxopyrrolidine-1-carboxylate (4.50 g, 0.0205 mol) and 4-bromo-2-methyl-2-butene (4.75 mL, 0.0412 mol) in 25.0 mL of saturated ammonium chloride and tetrahydrofuran (4.75 mL, 0.0586 mol) was added zinc (2.70 g, 0.0412 mol) at rt. Soon after stirring was started, gas and heat were evolved. After 45 min., the resulting light grey mixture was filtered through celite. Layers of the filtrate were separated and the aqueous layer of the filtrate was extracted with EtOAc. The organic layers were combined, washed with brine, dried and evaporated in-vacuo. The residue was purified on silica gel, eluting with 0 to 40% EtOAc in hexane, to give the desired product. LCMS (M+Na) 290.2.

Workup

  1. temperaturegas and heat
  2. filtrationthe resulting light grey mixture was filtered through celite
  3. customLayers of the filtrate were separated
  4. extractionthe aqueous layer of the filtrate was extracted with EtOAc
  5. washwashed with brine
  6. customdried
  7. customevaporated in-vacuo
  8. customThe residue was purified on silica gel
  9. washeluting with 0 to 40% EtOAc in hexane

Sources & evidence

ORD record
ord-eae8bd0b18294d0daea5afda98a55a45
Source dataset
uspto-grants-2010_08
Patent number
US07776874B2

Reaction notes

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