Sulfuric Acid → (2S,4R)-2-(allyloxycarbonylmethyloxymethyl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 703576Notes

Reaction equation

HRID 703576 reaction equation
[C:1]([CH2:4][O:5][CH2:6][C@@H:7]1[CH2:11][C@@H:10]([O:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH2:9][N:8]1[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=1)=[O:18])([OH:3])=[O:2].S(=O)(=O)(O)O.C(N(CC)CC)C.[CH2:42](O)[CH:43]=[CH2:44]>C(OCC)(=O)C>[CH2:44]([O:2][C:1]([CH2:4][O:5][CH2:6][C@@H:7]1[CH2:11][C@@H:10]([O:12][S:13]([CH3:16])(=[O:14])=[O:15])[CH2:9][N:8]1[C:17]([O:19][CH2:20][C:21]1[CH:22]=[CH:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=1)=[O:18])=[O:3])[CH:43]=[CH2:42]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 7858Allyl AlcoholHCID 8471TriethylamineHCID 18631935(2S,4R)-2-(carboxymethyloxymethyl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Product 1

HCID 18642547(2S,4R)-2-(allyloxycarbonylmethyloxymethyl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of (2S,4R)-2-(carboxymethyloxymethyl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (5.20 g) in allyl alcohol (52 ml) was refluxed in the presence of sulfuric acid (0.5 ml) for 5 hours. After cooling, triethylamine (3.14 ml) was added to the mixture. The mixture was concentrated under reduced pressure to give a syrup. The syrup was dissolved in ethyl acetate (100 ml), washed in turn with water (100 ml) and brine (100 ml), dried over magnesium sulfate, and concentrated under reduced pressure to give (2S,4R)-2-(allyloxycarbonylmethyloxymethyl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (6.05 g).

Workup

  1. temperatureAfter cooling
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customto give a syrup
  4. washwashed in turn with water (100 ml) and brine (100 ml)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-78fb0f202c47449789dca84891859557
Source dataset
uspto-grants-1991_01
Patent number
US04983596

Reaction notes

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