HCID 20741423, compound → HCID 20741403, compound

HRID 348398Notes

Reaction equation

HRID 348398 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C@H:16]1[CH2:20][N:19]([C@@H:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH3:22])[C:18](=O)[CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>O1CCCC1>[C:1]([O:5][C:6]([NH:8][CH:9]([C@@H:16]1[CH2:17][CH2:18][N:19]([C@@H:21]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH3:22])[CH2:20]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 1

HCID 20741423HCID 20741423, compound

Product 1

HCID 20741403HCID 20741403, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, 1 mol/l borane-tetrahydrofuran complex (4.6 ml) was added dropwise to a tetrahydrofuran solution (10 ml) of 4-(R)-[1-tert-butoxycarbonylamino-1-phenylmethyl]-1-[1-(R)-phenylethyl]-2-pyrrolidone [F1] (600 mg, 1.52 mmol) under ice cooling, followed by stirring at room temperature for 13 hours. After removal of the solvent under reduced pressure, 80% water-containing ethanol (15 ml) and triethylamine (3 ml) were added to the residue and the mixture was heated under reflux for 5 hours. After cooling on standing, the solvent was removed under reduced pressure and chloroform (30 ml) was added to the residue. The solution was washed with water (10 ml) and saturated saline (10 ml) and dried over anhydrous sodium sulfate. After removal of the solvent under reduced pressure, the residue was subjected to silica gel column chromatography. Elution with chloroform/methanol (20/1) afforded the title compound (510 mg, 88%) as colorless crystals.

Workup

  1. customAfter removal of the solvent under reduced pressure, 80% water-
  2. additioncontaining ethanol (15 ml) and triethylamine (3 ml)
  3. additionwere added to the residue
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 5 hours
  6. temperatureAfter cooling
  7. customthe solvent was removed under reduced pressure and chloroform (30 ml)
  8. additionwas added to the residue
  9. washThe solution was washed with water (10 ml) and saturated saline (10 ml)
  10. dry with materialdried over anhydrous sodium sulfate
  11. customAfter removal of the solvent under reduced pressure
  12. washElution with chloroform/methanol (20/1)

Sources & evidence

ORD record
ord-b5fa4900fd994a04a446b59917594da3
Source dataset
uspto-grants-2007_02
Patent number
US07176313B2

Reaction notes

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