Toluene → t-Butyl (3-(1-acetyl-pyrrolidin-2-yl)-4-benzyloxy-phenyl)-carbamate

HRID 13265Notes

Reaction equation

HRID 13265 reaction equation
C([N:4](C(C)C)CC)(C)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[C:27]([N:30]1[CH2:34][CH2:33][CH2:32][CH:31]1[C:35]1[CH:36]=[C:37]([CH:41]=[CH:42][C:43]=1[O:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)C(O)=O)(=[O:29])[CH3:28].[C:52](=[O:55])(O)[O-:53].[Na+].[C:57]1([CH3:63])[CH:62]=CC=C[CH:58]=1>CC(O)(C)C>[C:27]([N:30]1[CH2:34][CH2:33][CH2:32][CH:31]1[C:35]1[CH:36]=[C:37]([NH:4][C:52](=[O:55])[O:53][C:57]([CH3:63])([CH3:62])[CH3:58])[CH:41]=[CH:42][C:43]=1[O:44][CH2:45][C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1)(=[O:29])[CH3:28]

Participants

7

Reactant 5

HCID 1140TolueneHCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 516892Sodium BicarbonateHCID 23145661HCID 23145661, compound

Product 1

HCID 86619203t-Butyl (3-(1-acetyl-pyrrolidin-2-yl)-4-benzyloxy-phenyl)-carbamate

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

3.0 ml of diisopropylethylamine and 3.8 ml of diphenylphosphoryl azide were added in order to a solution of 5 g of 3-(1-acetyl-pyrrolidin-2-yl)-4-benzyloxybenzoic acid in a mixture of 15 ml of toluene and 15 ml of 2-methyl-2-propanol, and the reaction liquid was heated overnight under reflux. After cooled, saturated saline and aqueous saturated sodium bicarbonate were added to the reaction liquid, and this was extracted with ethyl acetate, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/0 to 1/1 to 0/1) to obtain the entitled compound as a colorless amorphous substance.

Workup

  1. customthe reaction liquid
  2. temperaturewas heated overnight
  3. temperatureunder reflux
  4. temperatureAfter cooled
  5. extractionthis was extracted with ethyl acetate
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customThe solvent was evaporated away under reduced pressure
  8. customthe resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/0 to 1/1 to 0/1)
  9. customto obtain the entitled compound as a colorless amorphous substance

Sources & evidence

ORD record
ord-e9b7a71fe29540f9aa2942b9086877ac
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

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