4-Bromophenacyl bromide → HCID 86682811, compound

HRID 1524252Notes

Reaction equation

HRID 1524252 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][O:14][CH3:15])[CH2:10][C@H:9]1[C:16]([OH:18])=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][CH:24]=1)=[O:22].C(N(CC)CC)C>CC#N.CCOC(C)=O>[CH3:15][O:14][CH2:13][C@@H:11]1[CH2:12][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C@H:9]([C:16]([O:18][CH2:20][C:21]([C:23]2[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][CH:24]=2)=[O:22])=[O:17])[CH2:10]1

Participants

6

Reactant 3

HCID 74544-Bromophenacyl bromideHCID 8471TriethylamineHCID 696720591,2-Pyrrolidinedicarboxylic acid, 4-(methoxymethyl)-, 1-(1,1-dimethylethyl) ester, (2S,4S)-

Product 1

HCID 86682811HCID 86682811, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2S,4S)-1-(tert-butoxycarbonyl)-4-(methoxymethyl)pyrrolidine-2-carboxylic acid (2.00 g, 7.2 mmol) and 2-bromo-1-(4-bromophenyl)ethanone (2.02 g, 7.8 mmol) in MeCN (35 mL) was added triethylamine (1.1 mL, 7.9 mmol). The solution was stirred at room temperature for 24 h and diluted with EtOAc. The solution was washed aqueous HCl (1M) and brine. The aqueous layer was backextracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated in vacuo to provide (2S,4S)-2-(2-(4-bromophenyl)-2-oxoethyl) 1-tert-butyl 4-(methoxymethyl)pyrrolidine-1,2-dicarboxylate (3.3 g, 100%).

Workup

  1. washThe solution was washed aqueous HCl (1M) and brine
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eeeb50f0d4be476d977550236a2f5f81
Source dataset
uspto-grants-2015_07
Patent number
US09079887B2

Reaction notes

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