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 417679Notes

Reaction equation

HRID 417679 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, 3.22 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-54dd25ed1770486db11fd574a30c9fe6
Source dataset
uspto-grants-2012_01
Patent number
US08088368B2

Reaction notes

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