Allyl bromide → HCID 58118695, compound

HRID 1615797Notes

Reaction equation

HRID 1615797 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@@:9]2([CH3:27])[NH:18][C:17](=[O:19])[C:12]3([CH2:16][CH2:15][CH2:14][CH2:13]3)[N:11]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1.[H-].[Na+].[CH2:30](Br)[CH:31]=[CH2:32]>CN(C=O)C>[CH2:32]([N:18]1[C:17](=[O:19])[C:12]2([CH2:16][CH2:15][CH2:14][CH2:13]2)[N:11]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:10][C@:9]1([C:4]1[CH:5]=[C:6]([F:8])[CH:7]=[C:2]([F:1])[CH:3]=1)[CH3:27])[CH:31]=[CH2:30]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 70804527HCID 70804527, compound

Product 1

HCID 58118695HCID 58118695, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of tert-butyl (8R)-8-(3,5-difluorophenyl)-8-methyl-10-oxo-6,9-diazaspiro[4.5]decane-6-carboxylate (500 mg, 1.314 mmol) in 2 ml of DMF was added to a suspension of sodium hydride (49.8 mg, 1.971 mmol). When the gas evolution had ceased, allyl bromide (0.171 mL, 1.971 mmol) was added to the ice cooled solution. After 18 hours, the reaction was quenched with brine and extracted with ethyl acetate (3×30 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The oily residue was purified on silica gel, eluting with a gradient of ethyl acetate:hexanes—0:100 to 50:50. The clean fractions were concentrated in vacuo to yield the title compound. MS: m/z=421 (M+1).

Workup

  1. customthe reaction was quenched with brine
  2. extractionextracted with ethyl acetate (3×30 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe oily residue was purified on silica gel
  8. washeluting with a gradient of ethyl acetate
  9. concentrationThe clean fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-83af7e638c764b3b9e5f22e609681b2d
Source dataset
uspto-grants-2014_07
Patent number
US08765759B2

Reaction notes

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