Triethylamine → 4,4-Difluoro-pyrrolidine-1,2-dicarboxylic acid 2-[2-(6-bromo-naphthalen-2-yl)-2-oxo-ethyl]ester 1-tert-butyl ester

HRID 1185895Notes

Reaction equation

HRID 1185895 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Br:15])[CH:11]=2)[CH:6]=1)=[O:4].[C:16]([O:20][C:21]([N:23]1[CH2:27][C:26]([F:29])([F:28])[CH2:25][CH:24]1[C:30]([OH:32])=[O:31])=[O:22])([CH3:19])([CH3:18])[CH3:17].CCN(CC)CC>CC#N>[C:16]([O:20][C:21]([N:23]1[CH2:27][C:26]([F:28])([F:29])[CH2:25][CH:24]1[C:30]([O:32][CH2:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Br:15])[CH:11]=2)[CH:6]=1)=[O:4])=[O:31])=[O:22])([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 126988982-Bromo-1-(6-bromonaphthalen-2-yl)ethanoneHCID 235125141-((Tert-butoxy)carbonyl)-4,4-difluoropyrrolidine-2-carboxylic acid

Product 1

HCID 666208644,4-Difluoro-pyrrolidine-1,2-dicarboxylic acid 2-[2-(6-bromo-naphthalen-2-yl)-2-oxo-ethyl]ester 1-tert-butyl esterYield 83%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Bromo-1-(6-bromo-naphthalen-2-yl)-ethanone (1 g, 3.07 mmol) and 4,4-Difluoro-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (849 mg, 3.38 mmol) were suspended in MeCN (15 mL) and treated with Et3N (0.45 mL, 122 mmol). After stirring o/n, the reaction mixture was concentrated. The resulting residue was dissolved in EtOAc and washed with water, saturated aqueous NaHCO3 and brine. The organic layer was dried over MgSO4, filtered and concentrated. The crude material was purified by silica column chromatography (0% to 20% EtOAc/Hex) to provide the title compound (1.27 g, 83%).

Workup

  1. concentrationwas concentrated
  2. dissolutionThe resulting residue was dissolved in EtOAc
  3. washwashed with water, saturated aqueous NaHCO3 and brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by silica column chromatography (0% to 20% EtOAc/Hex)

Sources & evidence

ORD record
ord-4adfd7ad403c413a84b066dc3f05a64f
Source dataset
uspto-grants-2014_03
Patent number
US08669234B2

Reaction notes

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