Methanol → HCID 15056159, compound

HRID 1650854Notes

Reaction equation

HRID 1650854 reaction equation
[BH4-].[Na+].B(F)(F)F.CCOCC.[OH:12][C@H:13]1[CH2:17][N:16]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=2)=[O:19])[C@H:15]([CH2:31][N:32]2[C:36](=O)[CH:35]([CH3:38])[NH:34][C:33]2=[O:39])[CH2:14]1.CO>O1CCCC1>[OH:12][C@H:13]1[CH2:17][N:16]([C:18]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]([N+:28]([O-:30])=[O:29])=[CH:26][CH:27]=2)=[O:19])[C@H:15]([CH2:31][N:32]2[CH2:36][CH:35]([CH3:38])[NH:34][C:33]2=[O:39])[CH2:14]1

Participants

6

Reactant 4

HCID 887MethanolHCID 8000Boron trifluoride etherateHCID 4311764Sodium borohydrideHCID 15056158HCID 15056158, compound

Product 1

HCID 15056159HCID 15056159, compoundYield 47.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium borohydride (1.81 g) in tetrahydrofuran (50 ml) was dropwise added boron trifluoride etherate (23.4 ml) under ice-cooling and the mixture was stirred at the same temperature for 15 minutes. To this solution was added a solution of (2S,4R)-4-hydroxy-2-(4-methyl-2,5-dioxoimidazolidin-1-yl)methyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (9.37 g) in tetrahydrofuran (50 ml) under ice-cooling and the mixture was stirred at ambient temperature overnight. To the reaction mixture was dropwise added methanol (30 ml) and the mixture was filtered. The filtrate was evaporated in vacuo. The resulting residue was dissolved in methanol (100 ml) and concentrated hydrochloric acid (5 ml) and the solution was allowed to stand at ambient temperature for 3 hours. The reaction mixture was evaporated in vacuo and dissolved in ethyl acetate (300 ml). The solution was washed successively with saturated aqueous sodium hydrogen carbonate and aqueous sodium chloride, dried over magnesium sulfate and evaporated in vacuo. The resulting residue was chromatographed on silica gel (150 g) eluting with a mixture of chloroform and methanol (19:1, V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2S,4R)-4-hydroxy-2-(4-methyl-2-oxoimidazolidin-1-yl)methyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (4.31 g).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred at ambient temperature overnight
  4. filtrationthe mixture was filtered
  5. customThe filtrate was evaporated in vacuo
  6. dissolutionThe resulting residue was dissolved in methanol (100 ml)
  7. waitto stand at ambient temperature for 3 hours
  8. customThe reaction mixture was evaporated in vacuo
  9. dissolutiondissolved in ethyl acetate (300 ml)
  10. washThe solution was washed successively with saturated aqueous sodium hydrogen carbonate and aqueous sodium chloride
  11. dry with materialdried over magnesium sulfate
  12. customevaporated in vacuo
  13. customThe resulting residue was chromatographed on silica gel (150 g)
  14. washeluting with a mixture of chloroform and methanol (19:1, V/V)
  15. additionThe fractions containing the desired compound
  16. customwere collected
  17. customevaporated in vacuo

Sources & evidence

ORD record
ord-648e3c8ffbc647289b802d317618571d
Source dataset
uspto-grants-1990_05
Patent number
US04925838

Reaction notes

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