Ethanol → HCID 68585258, compound

HRID 17637Notes

Reaction equation

HRID 17637 reaction equation
[CH3:1][N:2]([C@@:10]1([CH3:24])[CH2:14][C:13](=O)[N:12]([C@@H:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH3:17])[CH2:11]1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].C(O)C.C(N(CC)CC)C.O>O1CCCC1>[CH3:1][N:2]([C@@:10]1([CH3:24])[CH2:14][CH2:13][N:12]([C@@H:16]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH3:17])[CH2:11]1)[C:3](=[O:9])[O:4][C:5]([CH3:6])([CH3:7])[CH3:8]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 8471TriethylamineHCID 68585159HCID 68585159, compound

Product 1

HCID 68585258HCID 68585258, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The above-mentioned tert-butyl methyl-{(3S)-3-methyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidin-3-yl}carbamate (3.94 g, 11.9 mmol) was dissolved in tetrahydrofuran (120 ml), then with cooling with ice, borane/tetrahydrofuran complex (29.6 ml 35.6 mmol) was added, followed by stirring at room temperature for 17 hours. Ethanol (36 ml), triethylamine (12 ml) and water (12 ml) were added to the reaction liquid, followed by stirring in an oil bath at 80° C. for 2 hours. The reaction liquid was concentrated under reduced pressure, partitioned with ethyl acetate and water, and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, the insoluble matter was separated by filtration, and the residue obtained by concentration was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=1:1, v/v) to obtain tert-butyl methyl-{(3S)-3-methyl-1-[(1R)-1-phenylethyl]pyrrolidin-3-yl}carbamate (2.44 g, 65%) as a colorless oily substance.

Workup

  1. temperaturewith cooling with ice, borane/tetrahydrofuran complex (29.6 ml 35.6 mmol)
  2. additionwas added
  3. stirringby stirring in an oil bath at 80° C. for 2 hours
  4. customThe reaction liquid
  5. concentrationwas concentrated under reduced pressure
  6. custompartitioned with ethyl acetate and water
  7. extractionthe aqueous layer was extracted with ethyl acetate
  8. washThe organic layer was washed with saturated brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. customthe insoluble matter was separated by filtration
  11. customthe residue obtained by concentration
  12. customwas purified by silica gel column chromatography (eluent, n-hexane

Sources & evidence

ORD record
ord-f93e5fd9c3374203b48ace4d02fd9839
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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