Toluene → (2S,4R)-1-benzyloxycarbonyl-2-[{3-(ethoxycarbonyl)-2-propenyl}oxymethyl]-4-methanesulfonyloxypyrrolidine

HRID 703585Notes

Reaction equation

HRID 703585 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]CC=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[CH:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])C=CC=CC=1.[C:51]1(C)C=CC=C[CH:52]=1>>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16][S:17]([CH3:20])(=[O:18])=[O:19])[CH2:13][C@H:12]1[CH2:21][O:22][CH2:51][CH:52]=[CH:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 18642544(2S,4R)-1-benzyloxycarbonyl-2-(2-oxoethyl)oxymethyl-4-methanesulfonyloxypyrrolidine

Product 1

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

Procedure

A solution of (2S,4R)-1-benzyloxycarbonyl-2-(2-oxoethyl)oxymethyl-4-methanesulfonyloxypyrrolidine (15.7 g) and ethyl 2-triphenylphosphoranylideneacetate (16.2 g) in toluene (150 ml) was heated under refluxing for 3 hours. The solvent was removed in vacuo to give a residue, which was chromatographed on silica gel (700 ml) eluting with a mixture of hexane and ethyl acetate (2:1-1:1 V/V) to give (2S,4R)-1-benzyloxycarbonyl-2-[{3-(ethoxycarbonyl)-2-propenyl}oxymethyl]-4-methanesulfonyloxypyrrolidine (12.86 g).

Workup

  1. temperatureunder refluxing for 3 hours
  2. customThe solvent was removed in vacuo
  3. customto give a residue, which
  4. customwas chromatographed on silica gel (700 ml)
  5. washeluting with a mixture of hexane and ethyl acetate (2:1-1:1 V/V)

Sources & evidence

ORD record
ord-6f445a3d2bf14073aef1c494274f9e58
Source dataset
uspto-grants-1991_01
Patent number
US04983596

Reaction notes

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