HCID 20741423, compound → HCID 20741403, compound

HRID 2417245Notes

Reaction equation

HRID 2417245 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 and under ice-cooling, 1 M borane-tetrahydrofuran complex (4.6 ml) was added dropwise to tetrahydrofuran solution (10 ml) of 4-(R)-[1-tert-butoxycarbonylamino-1-phenylmethyl]-1-[1-(R)-phenylethyl]-2-pyrrolidone [α](600 mg, 1.52 mmol), and the mixture was stirred at room temperature for 13 hours. After evaporation of the solvent under a reduced pressure, the residue was mixed with 80% aqueous 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 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 residue was subjected 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. temperatureIn an atmosphere of nitrogen and under ice-cooling
  2. customAfter evaporation of the solvent under a reduced pressure
  3. additionthe residue was mixed with 80% aqueous 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 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-3025cec22f564d9393c31e8b1a057bdc
Source dataset
uspto-grants-2004_11
Patent number
US06825353B2

Reaction notes

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