Water → HCID 86701852, compound

HRID 1844091Notes

Reaction equation

HRID 1844091 reaction equation
[NH:1]1[C:5](=[O:6])[CH2:4][C@H:3]2[CH2:7][C:8]3[C:13]([C@@H:2]12)=[CH:12][CH:11]=[CH:10][CH:9]=3.[H-].[Na+].[CH2:16](Br)[CH:17]=[CH2:18].O>CN(C=O)C>[CH2:18]([N:1]1[C:5](=[O:6])[CH2:4][C@H:3]2[CH2:7][C:8]3[C:13]([C@@H:2]12)=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:17]=[CH2:16]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 67975452HCID 67975452, compound

Product 1

HCID 86701852HCID 86701852, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (3aR,8bS)-3,3a,4,8b-tetrahydro-1H-indeno[1,2-b]pyrrol-2-one (1.00 g, 5.77 mmol) in DMF (10 mL) was added at 0° C. sodium hydride (60% in mineral oil, 0.254 g, 6.35 mmol). The solution was stirred for 1 h at 0° C. and allyl bromide (1.41 g, 2 equiv., 1.01 mL, 11.5 mmol) was added. The solution was stirred for 18 h at room temperature and water was added. The mixture was extracted with ethyl acetate and washed with water and brine. The solvents were removed in vacuo and the residue was purified by flash chromatography eluting with cyclohexane and ethyl acetate (50:50) to give (3aR,8bS)-1-allyl-3,3a,4,8b-tetrahydroindeno[1,2-b]pyrrol-2-one F22 (0.910 g, 0.910 g, 4.27 mmol, 73.9% Yield) as a colourless oil. LCMS (method A) 1.51 min; ES+: 214 (M+H+).

Workup

  1. stirringThe solution was stirred for 18 h at room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with water and brine
  4. customThe solvents were removed in vacuo
  5. customthe residue was purified by flash chromatography
  6. washeluting with cyclohexane and ethyl acetate (50:50)

Sources & evidence

ORD record
ord-b9d23676239745139aa25daea64df46e
Source dataset
uspto-grants-2015_02
Patent number
US08946280B2

Reaction notes

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