HCID 20741423, compound → HCID 20741403, compound

HRID 1883962Notes

Reaction equation

HRID 1883962 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

In an atmosphere of nitrogen, 1 M borane-tetrahydrofuran complex (4.6 ml) was added dropwise to tetrahydrofuran (10 ml) solution of 4-(R)-[1-tert-butoxycarbonylamino-1-phenylmethyl]-1-[1-(R)-phenyl ethyl]-2-pyrrolidone [F1] (600 mg, 1.52 mmol) under ice-cooling, and then the mixture was stirred at room temperature for 13 hours. After evaporation of the solvent under a reduced pressure, the resulting residue was mixed with 80% hydrous ethanol (15 ml) and triethylamine (3 ml) and heated under reflux for 5 hours. After spontaneous cooling, the solvent was evaporated under a reduced pressure, and chloroform (30 ml) was added to the resulting residue. This was washed with water (10 ml) and saturated brine (10 ml) and dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure and the resulting residue was applied to a silica gel column chromatography. By eluting with chloroform:methanol (20:1), 510 mg (88%) of the title compound was obtained as colorless crystals.

Workup

  1. temperaturecooling
  2. customAfter evaporation of the solvent under a reduced pressure
  3. additionthe resulting residue was mixed with 80% hydrous ethanol (15 ml) and triethylamine (3 ml)
  4. temperatureheated
  5. temperatureunder reflux for 5 hours
  6. customAfter spontaneous cooling, the solvent was evaporated under a reduced pressure, and chloroform (30 ml)
  7. additionwas added to the resulting residue
  8. washThis was washed with water (10 ml) and saturated brine (10 ml)
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe solvent was evaporated under a reduced pressure
  11. washBy eluting with chloroform:methanol (20:1)

Sources & evidence

ORD record
ord-8272a421dbfb4814b7a1123836df5a14
Source dataset
uspto-grants-2004_07
Patent number
US06762181B1

Reaction notes

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