Methanol → HCID 15056157, compound

HRID 1650851Notes

Reaction equation

HRID 1650851 reaction equation
[BH4-].[Na+].B(F)(F)F.CCOCC.[OH:12][CH2:13][CH2:14][N:15]1[CH2:19][CH2:18][N:17]([C:20]([C@@H:22]2[CH2:26][C@@H:25]([O:27][S:28]([CH3:31])(=[O:30])=[O:29])[CH2:24][N:23]2[C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][CH:37]=2)=[O:33])=O)[C:16]1=[O:45].CO>O1CCCC1.C(OCC)(=O)C>[OH:12][CH2:13][CH2:14][N:15]1[CH2:19][CH2:18][N:17]([CH2:20][C@@H:22]2[CH2:26][C@@H:25]([O:27][S:28]([CH3:31])(=[O:30])=[O:29])[CH2:24][N:23]2[C:32]([O:34][CH2:35][C:36]2[CH:37]=[CH:38][C:39]([N+:42]([O-:44])=[O:43])=[CH:40][CH:41]=2)=[O:33])[C:16]1=[O:45]

Participants

7

Reactant 4

HCID 887MethanolHCID 8000Boron trifluoride etherateHCID 4311764Sodium borohydrideHCID 57179567HCID 57179567, compound

Product 1

HCID 15056157HCID 15056157, compoundYield 58.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of sodium borohydride (0.71 g) in tetrahydrofuran (25 ml) was added dropwise boron trifluoride etherate (11.8 ml) under ice-cooling and stirred at the same temperature for 10 minutes. To the mixture was added a solution of (2S,4R)-2-[3-(2-hydroxyethyl)-2-oxoimidazolidin-1-yl]carbonyl-4-methanesulfonyloxy1-(4-nitrobenzyloxycarbonyl)pyrrolidine (4.73 g) in tetrahydrofuran (50 ml) and the mixture was stirred at ambient temperature overnight. To the reaction mixture was added dropwise methanol (60 ml) under ice-cooling and evaporated in vacuo. The resulting residue was dissolved in methanol (30 ml) and conc. hydrochloric acid (1 ml) and stirred at ambient temperature for 3 hours. The reaction mixture was evaporated in vacuo to give a residue. The residue was dissolved in ethyl acetate (100 ml) and the solution was washed with saturated aqueous sodium hydrogen carbonate and aqueous sodium chloride successively, dried over anhydrous 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-(2-hydroxyethyl)-2-oxoimidazolidin-1-yl]methyl-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (2.70 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at ambient temperature overnight
  3. temperaturecooling
  4. customevaporated in vacuo
  5. dissolutionThe resulting residue was dissolved in methanol (30 ml)
  6. stirringconc. hydrochloric acid (1 ml) and stirred at ambient temperature for 3 hours
  7. customThe reaction mixture was evaporated in vacuo
  8. customto give a residue
  9. washthe solution was washed with saturated aqueous sodium hydrogen carbonate and aqueous sodium chloride successively
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customevaporated in vacuo
  12. customThe resulting residue was chromatographed on silica gel (100 g)
  13. washeluting with a mixture of chloroform and methanol (19:1, V/V)
  14. additionThe fractions containing the desired compound
  15. customwere collected
  16. customevaporated in vacuo

Sources & evidence

ORD record
ord-0460d3fbde2b4f8faf66bba8c103016f
Source dataset
uspto-grants-1990_05
Patent number
US04925838

Reaction notes

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