Boron trifluoride etherate → HCID 15086216, compound

HRID 1613990Notes

Reaction equation

HRID 1613990 reaction equation
[BH4-].[Na+].B(F)(F)F.CCOCC.[O:12]=[C:13]1[N:17]([CH2:18][C@@H:19]2[CH2:23][C@@H:22]([OH:24])[CH2:21][N:20]2[C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][CH:30]=2)=[O:26])[C:16](=O)[CH2:15][NH:14]1>O1CCCC1>[OH:24][C@H:22]1[CH2:21][N:20]([C:25]([O:27][CH2:28][C:29]2[CH:30]=[CH:31][C:32]([N+:35]([O-:37])=[O:36])=[CH:33][CH:34]=2)=[O:26])[C@H:19]([CH2:18][N:17]2[CH:16]=[CH:15][NH:14][C:13]2=[O:12])[CH2:23]1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 4311764Sodium borohydrideHCID 67834994HCID 67834994, compound

Product 1

HCID 15086216HCID 15086216, compoundYield 4.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium borohydr-ide (6.03 g) in tetrahydrofuran (270 ml) was added boron trifluoride etherate (72 ml) at 0° C. under stirring. After stirring for 10 minutes, to the suspension was added a solution of (2S,4R)-2-(2,4-dioxoimidazolidin-3-yl)methyl-4-hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (27.3 g) obtained in Preparation 10 in tetrahydrofuran (140 ml) and the mixture was stirred for 14 hours at ambient temperature. This reaction mixture was evaporated in vacuo and to the residue was added a solution of conc. hydrochloric acid (31 ml) in methanol (400 ml). After standing for 12 hours at ambient temperature, the solution was evaporated in vacuo and the resulting residue was poured into saturated aqueous sodium hydrogen carbonate (450 ml). The aqueous layer was extracted three times with a mixture of ethyl acetate (200 ml) and tetrahydrofuran (200 ml) and evaporated in vacuo. The resulting residue was chromatographed on silica gel (600 ml) eluting with a mixture of methanol and dichloromethane (5:95, V/V) to give (2 S,4R)-4-hydroxy-1-(4-nitrobenzyloxycarbonyl)-2-(2-oxo-4-imidazolin-1-yl)methyl pyrrolidine (1.11 g).

Workup

  1. stirringAfter stirring for 10 minutes, to the suspension
  2. stirringthe mixture was stirred for 14 hours at ambient temperature
  3. customThis reaction mixture was evaporated in vacuo and to the residue
  4. additionwas added a solution of conc. hydrochloric acid (31 ml) in methanol (400 ml)
  5. customthe solution was evaporated in vacuo
  6. additionthe resulting residue was poured into saturated aqueous sodium hydrogen carbonate (450 ml)
  7. extractionThe aqueous layer was extracted three times
  8. additionwith a mixture of ethyl acetate (200 ml) and tetrahydrofuran (200 ml)
  9. customevaporated in vacuo
  10. customThe resulting residue was chromatographed on silica gel (600 ml)
  11. washeluting with a mixture of methanol and dichloromethane (5:95, V/V)

Sources & evidence

ORD record
ord-5a68287bc6164497bf4406625ef1346b
Source dataset
uspto-grants-1993_03
Patent number
US05194624

Reaction notes

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