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

HRID 1876877Notes

Reaction equation

HRID 1876877 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-carboxylateYield 88%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 25517Ammonium ChlorideSolvent

Procedure

To a suspension of benzyl 3-oxopyrrolidine-1-carboxylate (4.50 g, 0.0205 mol), 4-bromo-2-methyl-2-butene (4.75 mL, 0.0412 mol) in 25.0 mL saturated ammonium chloride and tetrahydrofuran (4.75 mL, 0.0586 mol), at room temperature, was added zinc (2.70 g, 0.0412 mol). As soon as stirring was started, gas and heat were evolved. After 30 to 45 min, the resulting light grey mixture was filtered through celite. The filtrate was extracted with EtOAc. The organic layers were combined, washed with brine, dried and evaporated to dryness. The residue was purified on silica gel, eluting with 0 to 40% EtOAc in hexanes, to provide the desired product (5.22 g, 87.89%). LCMS (M+H) 290.2.

Workup

  1. temperaturegas and heat
  2. filtrationthe resulting light grey mixture was filtered through celite
  3. extractionThe filtrate was extracted with EtOAc
  4. washwashed with brine
  5. customdried
  6. customevaporated to dryness
  7. customThe residue was purified on silica gel
  8. washeluting with 0 to 40% EtOAc in hexanes

Sources & evidence

ORD record
ord-5bb1d35cb6eb4a4bb096562acceff77a
Source dataset
uspto-grants-2012_11
Patent number
US08309718B2

Reaction notes

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