Sodium Hydroxide → HCID 86746064, compound

HRID 846697Notes

Reaction equation

HRID 846697 reaction equation
[CH2:1]([NH:8][C:9](=[O:11])[OH:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:12]1[CH2:16][CH:15]=[CH:14][CH2:13]1.ClC1C=CC=C(C(OO)=[O:25])C=1.S(=O)(O)[O-].[Na+].[OH-].[Na+]>C(Cl)Cl>[CH2:1]([NH:8][C:9](=[O:10])[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:25]1[CH:15]2[CH:14]1[CH2:13][NH:12][CH2:16]2

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 23665763Sodium BisulfiteHCID 86746065HCID 86746065, compound

Product 1

HCID 86746064HCID 86746064, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A 15.00 g (74 mmol) sample of the 3-pyrroline benzyl carbamate from Step 1a was dissolved in 200 mL of methylene chloride and cooled to 0° C. A 46.3 g (267 mmol) sample of m-chloroperbenzoic acid was dissolved in 500 mL of methylene chloride and added dropwise with stirring over a period of 1 hours. The flask was then equipped with a condenser and the temperature was increased to 45° C. for 18 hours. The solution was cooled to room temperature, 2 g of sodium bisulfite was added, the solution was stirred for 30 min then poured into 1 L of 1M NaOH. and washed in a separatory funnel. The methylene chloride was then washed with 2×500 mL portions of potassium carbonate solution, dried over anhydrous sodium sulfate, and the solvent was filtered and removed by evaporation under vacuum. to afford 14.26 g of 3,4-epoxypyrrolidine benzyl carbamate, MS (DCl) M/Z 220 (M+H), 237 (M+NH4); NMR (CDCl3) d 3.39 (ddd, 2H, J=6.0, 1.5, 13.5 Hz), 3.87 (dd, 2H, J=12, 15 Hz), 5.12 (d, 2, J=3 Hz), 7.35 (m, 5H).

Workup

  1. additionadded dropwise
  2. customThe flask was then equipped with a condenser
  3. temperaturethe temperature was increased to 45° C. for 18 hours
  4. temperatureThe solution was cooled to room temperature
  5. stirringthe solution was stirred for 30 min
  6. washand washed in a separatory funnel
  7. washThe methylene chloride was then washed with 2×500 mL portions of potassium carbonate solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationthe solvent was filtered
  10. customremoved by evaporation under vacuum

Sources & evidence

ORD record
ord-f1c68a81edaf4d6496155e4d14c5e909
Source dataset
uspto-grants-1992_08
Patent number
US05137892

Reaction notes

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