Water → HCID 66848216, compound

HRID 536589Notes

Reaction equation

HRID 536589 reaction equation
[CH3:1][Si](C)(C)[N-][Si](C)(C)C.[Na+].[C:11]([O:15][C:16]([N:18]1[CH2:22][C:21](=O)[CH2:20][C@H:19]1[CH2:24][O:25][C:26](=[O:36])[C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12].O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(C)C=CC=CC=1>[C:11]([O:15][C:16]([N:18]1[CH2:22][C:21](=[CH2:1])[CH2:20][C@H:19]1[CH2:24][O:25][C:26](=[O:36])[C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 962WaterHCID 2724254Sodium bis(trimethylsilyl)amideHCID 66848206HCID 66848206, compound2×

Product 1

HCID 66848216HCID 66848216, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

Methytriphenylphosphonium bromide (38 g, 106 mmol) dissolved in 300 ml of toluene was cooled to 0° C., then added sodium hexamethyldisilazide (48.3 ml, 93.7 mmol) was added dropwise. After 2 hours at room temperature, The temperature was cooled to 0° C., a solution of (S)-2-(4-nitro-benzoyloxymethyl)-4-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (intermediate 56, 15.5 g, 42.6 mmol) in 300 ml of toluene was added. After 10 minutes 500 ml of water was slowly added, then reaction was allowed to reach room temperature. The organic solvent was washed with brine (500 ml), dried (Na2SO4) and evaporated to obtain crude that was purified by silica gel chromatography (petroleum ether/ethyl acetate from 15/7 to 7/1). (S)-4-Methylene-2-(4-nitro-benzoyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester was obtained as yellow solid (6.82 g, yield 46%).

Workup

  1. temperatureThe temperature was cooled to 0° C.
  2. customreaction
  3. customto reach room temperature
  4. washThe organic solvent was washed with brine (500 ml)
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customto obtain crude that
  8. customwas purified by silica gel chromatography (petroleum ether/ethyl acetate from 15/7 to 7/1)

Sources & evidence

ORD record
ord-41c56eacdd4f470487824f1b119743c6
Source dataset
uspto-grants-2014_10
Patent number
US08859608B2

Reaction notes

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