Benzyl Bromide → HCID 117966886, compound

HRID 712810Notes

Reaction equation

HRID 712810 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12](=[O:13])[C:11]([CH3:15])([CH3:14])[CH2:10][C@@H:9]1[C:16]([OH:18])=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC(C)=O>[CH3:14][C:11]1([CH3:15])[C:12](=[O:13])[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C@@H:9]([C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:10]1

Participants

4

Reactant 2

HCID 7498Benzyl Bromide3×HCID 117966732HCID 117966732, compound

Product 1

HCID 117966886HCID 117966886, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of (R)-1-(tert-butoxycarbonyl)-4,4-dimethyl-5-oxopyrrolidine-2-carboxylic acid (D38) (320 mg, 1.24 mmol) in acetone (10 ml), TEA (0.35 ml, 2.49 mmol) and benzyl bromide (0.23 ml, 1.86 mmol) were added and the resulting mixture was stirred at RT for 18 hrs. TEA (0.35 ml, 2.49 mmol) and benzyl bromide (0.23 ml, 1.86 mmol) were added and the reaction stirred for 24 hrs prior addition of further TEA (0.35 ml, 2.49 mmol) and benzyl bromide (0.23 ml, 1.86 mmol). The final mixture was then refluxed for 18 hrs. Solvents were evaporated off and the resulting residue was re-dissolved in EtOAc, washed with water (3×10 ml), dried over Na2SO4 and evaporated in vacuo to afford a residue that was purified by Biotage SNAP-Si column (25 g) eluting with a mixture DCM/EtOAc from 100/0 to 90/10. Collected fractions after solvent evaporation afforded the title compound (D39) (260 mg).

Workup

  1. stirringthe reaction stirred for 24 hrs
  2. customSolvents were evaporated off
  3. dissolutionthe resulting residue was re-dissolved in EtOAc
  4. washwashed with water (3×10 ml)
  5. dry with materialdried over Na2SO4
  6. customevaporated in vacuo
  7. customto afford a residue that
  8. customwas purified by Biotage SNAP-Si column (25 g)
  9. washeluting with a mixture DCM/EtOAc from 100/0 to 90/10
  10. customCollected fractions after solvent evaporation

Sources & evidence

ORD record
ord-94d10e84fc35458da3496e340bd21601
Source dataset
uspto-grants-2015_11
Patent number
US09181279B2

Reaction notes

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