Ammonia → HCID 15023848, compound

HRID 2226499Notes

Reaction equation

HRID 2226499 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11](OS(C)(=O)=O)[CH:10]([O:18][CH2:19][C:20]([F:23])([F:22])[F:21])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH3:24]>CO>[NH2:24][CH:11]1[CH:10]([O:18][CH2:19][C:20]([F:23])([F:22])[F:21])[CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:12]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 15023847HCID 15023847, compound

Product 1

HCID 15023848HCID 15023848, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 3.95 g (0.011 mole) of 1-t-butoxycarbonyl-3-(2,2,2-trifluoroethoxy)-4-methylsulfonyloxypyrrolidine [prepared as described in step (a) above] and 100 ml of methanol containing 20% w/v ammonia was transferred to an autoclave and then stirred at 140° C. for 10 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and the residue was mixed with a saturated aqueous solution of sodium carbonate and extracted with ethyl acetate. The organic extract was dried over anhydrous sodium sulfate and concentrated by evaporation under reduced pressure. The residue was purified by column chromatography through silica gel using a 1:9 by volume mixture of ethanol and ethyl acetate as the eluent, to give 1.61 g of 3-amino-1-t-butoxycarbonyl-4-(2,2,2-trifluoroethoxy)pyrrolidine as a colorless oil. Mass Spectrum (CI): m/e 285 (M+ +1), 229 (M+ +1--CH2 =C(CH3)2).

Workup

  1. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  2. additionthe residue was mixed with a saturated aqueous solution of sodium carbonate
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customThe residue was purified by column chromatography through silica gel using a 1:9
  8. additionby volume mixture of ethanol and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-0c24263eec1f4a5ebdc9f0e32613f240
Source dataset
uspto-grants-1994_09
Patent number
US05348961

Reaction notes

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