Methanol → HCID 15056166, compound

HRID 1650856Notes

Reaction equation

HRID 1650856 reaction equation
[BH4-].[Na+].B(F)(F)F.CCOCC.[C:12]([N:15]1[CH2:19][CH2:18][N:17]([CH2:20][C@@H:21]2[CH2:25][C@@H:24]([O:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH2:23][N:22]2[C:31]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][CH:36]=2)=[O:32])[C:16]1=[O:44])(=O)[CH3:13].CO>O1CCCC1>[CH2:12]([N:15]1[CH2:19][CH2:18][N:17]([CH2:20][C@@H:21]2[CH2:25][C@@H:24]([O:26][S:27]([CH3:30])(=[O:28])=[O:29])[CH2:23][N:22]2[C:31]([O:33][CH2:34][C:35]2[CH:36]=[CH:37][C:38]([N+:41]([O-:43])=[O:42])=[CH:39][CH:40]=2)=[O:32])[C:16]1=[O:44])[CH3:13]

Participants

6

Reactant 4

HCID 887MethanolHCID 8000Boron trifluoride etherateHCID 4311764Sodium borohydrideHCID 15056165HCID 15056165, compound

Product 1

HCID 15056166HCID 15056166, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium borohydride (0.16 g) in tetrahydrofuran (11 ml) was dropwise added boron trifluoride etherate (2.83 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)-2-(3-acetyl-2-oxoimidazolidin-1-yl)methyl-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1.12 g) in tetrahydrofuran (2.83 ml) under ice-cooling and the mixture was stirred at ambient temperature overnight. To the reaction mixture was added dropwise methanol (30 ml) and the mixture was filtrated. The filtrate was evaporated in vacuo. The resulting residue was dissolved in methanol (30 ml) and conc. hydrochloric acid (0.5 ml) and the solution was allowed to stand at ambient temperature overnight. The reaction mixture was evaporated in vacuo and dissolved in ethyl acetate (50 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 (100 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)-2-(3-ethyl-2-oxoimidazolidin-1-yl)methyl-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1.04 g).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred at ambient temperature overnight
  4. filtrationthe mixture was filtrated
  5. customThe filtrate was evaporated in vacuo
  6. dissolutionThe resulting residue was dissolved in methanol (30 ml)
  7. waitto stand at ambient temperature overnight
  8. customThe reaction mixture was evaporated in vacuo
  9. dissolutiondissolved in ethyl acetate (50 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 (100 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-22e308244edf4d33a001919de785acb2
Source dataset
uspto-grants-1990_05
Patent number
US04925838

Reaction notes

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