Sodium Carbonate → HCID 71182917, compound

HRID 1891399Notes

Reaction equation

HRID 1891399 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH:11]3[CH2:13][C:14]4([CH2:19][CH:10]3[CH2:9]2)[O:18][CH2:17][CH2:16][O:15]4)=[C:4]([F:20])[CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl[C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29]>CC(C)=O>[CH2:31]([O:30][C:28]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:9][CH:10]3[CH2:19][C:14]4([CH2:13][CH:11]3[CH2:12]2)[O:15][CH2:16][CH2:17][O:18]4)=[C:4]([F:20])[CH:3]=1)=[O:29])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 86675641HCID 86675641, compound

Product 1

HCID 71182917HCID 71182917, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-(4-amino-2-fluorophenyl)-hexahydro-1H-spiro[cyclopenta[c]pyrrol-5,2′-[1,3]dioxolane] (74.7 mmol) prepared in the step 5 was dissolved in 300 ml of acetone, and 150 ml of a 10 wt % sodium carbonate aqueous solution was added. And then, the temperature was lowered to 0° C., 13.86 ml (97.1 mmol) of benzyl chloroformate was slowly added dropwise over 30 minutes, and the mixture was stirred for 12 hours while raising the temperature to room temperature. After the reaction was completed, the solvent was removed under reduced pressure, 300 ml of ethyl acetate was added, the mixture was washed with water and sodium chloride, and then, the organic layer was dried over magnesium sulfate and filtered and concentrated under reduced pressure. The concentrate was separated by column chromatography to obtain 24.1 g (78%) of the title compound, of which NMR data is as follows.

Workup

  1. customwas lowered to 0° C.
  2. customthe solvent was removed under reduced pressure, 300 ml of ethyl acetate
  3. additionwas added
  4. washthe mixture was washed with water and sodium chloride
  5. dry with materialthe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe concentrate was separated by column chromatography

Sources & evidence

ORD record
ord-02c41de4be9e4a9c816a7fbf79440ab3
Source dataset
uspto-grants-2013_08
Patent number
US08507540B2

Reaction notes

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