1,8-Diazabicyclo(5.4.0)undec-7-ene → (2S,4R)-1-benzyloxycarbonyl-2-[{3-(ethoxycarbonyl)-2-propenyl}oxymethyl]-4-methanesulfonyloxypyrrolidine

HRID 703583Notes

Reaction equation

HRID 703583 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH2:13][C@H:12]1[CH2:21][O:22][CH2:23][CH:24](OS(C)(=O)=O)[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N12CCCN=C1CCCCC2>O1CCCC1.C(OCC)(=O)C.O.Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH2:13][C@H:12]1[CH2:21][O:22][CH2:23][CH:24]=[CH:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 57247090(2S,4R)-1-benzyloxycarbonyl-2-[{3-(ethoxycarbonyl)-2-methanesulfonyloxypropyl}oxymethyl]-4-methanesulfonyloxypyrrolidine

Product 1

HCID 57248036(2S,4R)-1-benzyloxycarbonyl-2-[{3-(ethoxycarbonyl)-2-propenyl}oxymethyl]-4-methanesulfonyloxypyrrolidineYield 89.5%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2S,4R)-1-benzyloxycarbonyl-2-[{3-(ethoxycarbonyl)-2-methanesulfonyloxypropyl}oxymethyl]-4-methanesulfonyloxypyrrolidine (3.7 g) in tetrahydrofuran (40 ml) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (5.1 ml) at ambient temperature and the mixture was stirred for one hour. Removal of the solvent in vacuo gave an oil which was dissolved in a mixture of ethyl acetate (100 ml), water (50 ml) and 1N-hydrochloric acid (10 ml). The organic layer was separated, washed twice with brine (50 ml) and dried over magnesium sulfate. Evaporation of the solvent gave a residue, which was chromatographed on silica gel (200 ml) eluting with a mixture of hexane and ethyl acetate (1:1 V/V) to give (2S,4R)-1-benzyloxycarbonyl-2-[{3-[ethoxycarbonyl)-2-propenyl}oxymethyl]-4-methanesulfonyloxypyrrolidine (2.72 g).

Workup

  1. customRemoval of the solvent in vacuo
  2. customgave an oil which
  3. customThe organic layer was separated
  4. washwashed twice with brine (50 ml)
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation of the solvent
  7. customgave a residue, which
  8. customwas chromatographed on silica gel (200 ml)
  9. washeluting with a mixture of hexane and ethyl acetate (1:1 V/V)

Sources & evidence

ORD record
ord-934663fc26824a969fd5487d4591d234
Source dataset
uspto-grants-1991_01
Patent number
US04983596

Reaction notes

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