Trifluoroacetic acid → Ethyl 1-benzyl-4-(1-tert-butoxycarbonylaminocyclopropyl)-3-pyrroline-3-carboxylate

HRID 1954583Notes

Reaction equation

HRID 1954583 reaction equation
[CH2:1]([N:8]([CH2:15][Si](C)(C)C)[CH2:9]OCCCC)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]([O:24][C:25]([NH:27][C:28]1([C:31]#[C:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:30][CH2:29]1)=[O:26])([CH3:23])([CH3:22])[CH3:21].FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]([N:8]1[CH2:9][C:31]([C:28]2([NH:27][C:25]([O:24][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:26])[CH2:30][CH2:29]2)=[C:32]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:15]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 11097910N-Benzyl-1-butoxy-N-[(trimethylsilyl)methyl]methanamineHCID 21261039Ethyl 3-(1-tert-butoxycarbonylaminocyclopropyl)propiolate

Product 1

HCID 21261012Ethyl 1-benzyl-4-(1-tert-butoxycarbonylaminocyclopropyl)-3-pyrroline-3-carboxylateYield 83.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-Benzyl-N-(n-butoxymethyl)trimethylsilylmethylamine (2.006 g, 7.176 mmol) and ethyl 3-(1-tert-butoxycarbonylaminocyclopropyl)propiolate (1.136 g, 4.485 mmol) were dissolved in dry dichloromethane (9 ml) and, while stirring at room temperature, the solution was mixed with dichloromethane solution of 1.0 M trifluoroacetic acid (0.72 ml, 0.72 mmol). After 3 hours of stirring, the reaction solution was mixed with a saturated sodium bicarbonate aqueous solution (20 ml) and extracted with dichloromethane (20 ml×3). The organic layers were combined, washed with saturated brine (30 ml) and then dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the resulting residue was applied to a flash silica gel chromatography column and eluted with chloroform, to thereby obtain 1.449 g (83.6%) of the title compound as a colorless oil.

Workup

  1. stirringAfter 3 hours of stirring
  2. extractionextracted with dichloromethane (20 ml×3)
  3. washwashed with saturated brine (30 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. washeluted with chloroform

Sources & evidence

ORD record
ord-7bd1788326884d03ad5d30d5c1fc1580
Source dataset
uspto-grants-2000_09
Patent number
US06121285

Reaction notes

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